original_index int64 2 1.77M | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | date_of_experiment timestamp[ns]date | extracted_from_file stringclasses 489 values | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1 class | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 stringlengths 1 208 ⌀ | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 stringlengths 1 285 ⌀ | rxn_str stringlengths 87 6.12k | rxn_time float64 0 2.16k ⌀ | solvent_000 stringclasses 446 values | solvent_001 stringclasses 405 values | solvent_002 stringclasses 330 values | temperature float64 -230 30.1k ⌀ | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,327,015 | [K] | null | null | null | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | 2013-01-01T00:08:00 | true | Prop-2-ynyl 6-bromohexanoate (0.606 g, 2 mmol, 1 eq.) was added to a solution of phthalimide potassium salt (0.441 g, 2.4 mmol, 1.2 eq.) in 50 mL of DMF and stirred overnight under argon. CHCl3 was added to the solution flask and was transferred to a separatory funnel containing water. The aqueous layer was separated and twice extracted with CHCl3. The combined organic layers were twice extracted with water then the solvent was removed on a rotary evaporator. Remaining solvent was removed under high vacuum overnight to yield a brown oil. | C#CCOC(=O)CCCCCN1C(=O)c2ccccc2C1=O | null | C#CCOC(=O)CCCCCBr | O=C1NC(=O)c2ccccc21 | null | Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8].[K].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C(Cl)(Cl)Cl.O>CN(C=O)C>[C:14]1(=[O:24])[N:18]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12 | 8 | O | ClC(Cl)Cl | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
167,208 | O=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [Zn] | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | ord_dataset-fdef1f30cad64430bf05cf108d8004a2 | 1988-01-01T00:01:00 | true | To a stirred mixture of triphenylphosphine (40.7 g) and zinc powder (18.5 g) in methylene chloride (250 ml) was added carbontetrabromide (45 g) at 20°-30° C. Benzhydryl 7-phenylacetamido-3-formyl-2-cephem-4-carboxylate (10 g) was added portionwise to the above reaction mixture, and the mixture was stirred for 30 minutes at room temperature. Triphenylphosphine oxide was solidified by addition of ethyl acetate to the reaction mixture and removed by filtration. The residue left by removal of the solvents was chromatographed on silica gel. The elution with chloroform containing ethyl acetate (10%) gave benzhydryl 7-phenylacetamido-3-(2,2-dibromovinyl)-2-cephem-4-carboxylate (4.4 g). | O=C(Cc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)C(C=C(Br)Br)=CS[C@H]12 | null | BrC(Br)(Br)Br | O=CC1=CS[C@@H]2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)OC(c1ccccc1)c1ccccc1 | null | C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[C:25]1([CH2:31][C:32]([NH:34][CH:35]2[C:60](=[O:61])[N:37]3[CH:38]([C:44]([O:46][CH:47]([C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=4)[C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)=[O:45])[C:39]([CH:42]=O)=[CH:40][S:41][C@H:36]23)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.[Zn].C(OCC)(=O)C>[C:25]1([CH2:31][C:32]([NH:34][CH:35]2[C:60](=[O:61])[N:37]3[CH:38]([C:44]([O:46][CH:47]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C:54]4[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=4)=[O:45])[C:39]([CH:42]=[C:20]([Br:24])[Br:21])=[CH:40][S:41][C@H:36]23)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1 | 0.5 | CCOC(C)=O | ClCCl | null | 25 | 33.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
654,386 | Cl | O=C([O-])O | [Na+] | null | ord_dataset-fe016e2f90e741a590ad77fd5933161f | 2004-01-01T00:11:00 | true | A mixture of (R)-3-(5-acetoxyhexyl)-1,5-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (175 mg, 0.50 mmol), methanol (5 ml) and 12 M aqueous hydrochloric acid (1 ml) was stirred at room temperature for 18 hours and then treated with saturated aqueous sodium bicarbonate solution (10 ml). After concentrating under reduced pressure to remove the methanol, the aqueous mixture was extracted with ethyl acetate (20 ml). The extract was applied to a short column of silica gel and eluted with ethyl acetate to afford (R)-1,5-dimethyl-3-(5-hydroxyhexyl)pyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (50 mg, 32% yield) as a white powder. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.30-1.71 (m, 6H), 2.67 (s, 3H), 3.57 (s, 3H), 3.72-3.88 (m, 1H), 3.98 (t, 2H), 6.23 (s, 1H). | Cc1cc(=O)[nH]c2c1c(=O)n(CCCC[C@@H](C)O)c(=O)n2C | null | CC(=O)O[C@H](C)CCCCn1c(=O)c2c(C)cc(=O)[nH]c2n(C)c1=O | null | null | C([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([CH3:22])=[CH:18][C:19](=[O:21])[NH:20][C:13]=2[N:12]([CH3:23])[C:11]1=[O:24])(=O)C.Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:23][N:12]1[C:13]2[NH:20][C:19](=[O:21])[CH:18]=[C:17]([CH3:22])[C:14]=2[C:15](=[O:16])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:25])[C:11]1=[O:24] | 18 | CO | null | null | 25 | 32.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
60,950 | null | null | null | null | ord_dataset-912d62c1690b4ebfbe998c0c9baf88a8 | 1979-01-01T00:12:00 | true | From 4,5-dichloro-2-dichloromethylene-imidazole ("one-pot process"). 654 g (3 mol) of 4,5-dichloro-2-dichloromethyleneimidazole in a finely powdered form were added incrementally in the course of about one hour, to a mixture, which had been initially introduced, of 783 g (9 mol) of isopropylformamide and 162 g (9 mol) of water, while stirring and cooling slightly, whereupon the internal temperature rose to about 75° C. The reaction mixture was then heated to about 90°-110° C. for a further half hour. After cooling, the product was precipitated in water, filtered off, washed with water and dried. In this way, 566 g (85% of theory) of 4,5-dichloro-imidazole-2-carboxylic acid isopropylamide with a melting point of 150° C. were obtained. | CC(C)NC(=O)c1nc(Cl)c(Cl)[nH]1 | null | ClC1=NC(=C(Cl)Cl)N=C1Cl | CC(C)NC=O | null | [Cl:1][C:2]1[C:6]([Cl:7])=[N:5][C:4](=C(Cl)Cl)[N:3]=1.[CH:11]([NH:14][CH:15]=[O:16])([CH3:13])[CH3:12].O>>[CH:11]([NH:14][C:15]([C:4]1[NH:3][C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=1)=[O:16])([CH3:13])[CH3:12] | null | O | null | null | null | 85 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
222,885 | null | null | null | null | ord_dataset-59f453c3a3d34a89bfd97b6b8b151908 | 1991-01-01T00:02:00 | true | Condensation between 4-benzylpiperidine (438 mg) and 2,4-dibenzyloxybenzoic acid is carried out in the same manner as in Example 4, i) to obtain 1-(2,4-dibenzyloxybenzoyl)-4-benzylpiperidine (1.0 g) in the colorless oily form. | O=C(c1ccc(OCc2ccccc2)cc1OCc1ccccc1)N1CCC(Cc2ccccc2)CC1 | null | O=C(O)c1ccc(OCc2ccccc2)cc1OCc1ccccc1 | c1ccc(CC2CCNCC2)cc1 | null | [CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([O:21][C:22]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:22]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:28]=[CH:27][C:23]=1[C:24]([N:11]1[CH2:12][CH2:13][CH:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)=[O:25])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
397,878 | [K+] | [OH-] | null | null | ord_dataset-a4a191e812a64d0598ea918f047e8da7 | 1998-01-01T00:04:00 | true | A solution of 1,8-dichloro-3, 6-dioxaoctane (40 g) and potassium hydroxide (11.8 g) in ethylene glycol (100 ml) was stirred at 100° C. for 18 h. The mixture was then cooled, filtered and the residue washed with acetone (2×35 ml). The combined filtrate was then distilled to yield the product as a clear oil (13.5 g, 30%), b.p. 120°-122° C./0.2 mm Hg; I.r. (liquid film) 3430 cm-1. | OCCOCCOCCOCCCl | null | ClCCOCCOCCCl | OCCO | null | Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][Cl:10].[OH-].[K+].[CH2:13]([OH:16])[CH2:14][OH:15]>>[Cl:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:15][CH2:14][CH2:13][OH:16] | null | null | null | null | null | null | 30 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
332,283 | null | null | null | null | ord_dataset-1558660634294cc8ad7e01746e9083fd | 1996-01-01T00:06:00 | true | More specifically, following Tetrahedron Letters, 31, 6321-6324 (1990), trifluoromethanesulfonic anhydride (4) is reacted with 1,1-bi-2-naphthol (3) to form 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl (5). This compound (5) is reacted with phosphine oxide (6) in the presence of a palladium catalyst to form 2-phosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl (7). Compound (7) is then reduced in the presence of triethylamine, followed by hydrolysis of the reduction product to form 2-phosphino-2'-hydroxy-1,1'-binaphthyl (8). Further, this compound (8) is reacted with chlorophosphine (9) in the presence of triethylamine, whereby the phosphine compound (I) of the present invention is prepared. | Oc1ccc2ccccc2c1-c1c(P)ccc2ccccc12 | null | O=[PH2]c1ccc2ccccc2c1-c1c(OS(=O)(=O)C(F)(F)F)ccc2ccccc12 | null | null | [PH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[O:23]S(C(F)(F)F)(=O)=O)=O>C(N(CC)CC)C>[PH2:1][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[OH:23] | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,042,986 | CCOC(=O)c1nc2ccccc2c(=O)[nH]1 | NCc1ccnc(OCCCc2ncn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)c1 | null | null | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | 2011-01-01T00:03:00 | true | By a method similar to that in Example 22, and using, instead of ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate, ethyl 5-[3-(ethoxycarbonyl)phenyl]-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxylate obtained in Reference Example 82 and using, instead of 1-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methaneamine, 1-{3-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]oxy}ethyl)oxy]phenyl}methanamine obtained in Reference Example 32, the title compound was obtained as a white powder (132.7 mg, 58%). | CCOC(=O)c1cccc(-c2csc3nc(C(=O)NCc4cccc(OCCOc5nc[nH]n5)c4)[nH]c(=O)c23)c1 | null | CCOC(=O)c1cccc(-c2csc3nc(C(=O)OCC)[nH]c(=O)c23)c1 | NCc1cccc(OCCOc2ncn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)c1 | null | O=C1C2C(=CC=CC=2)N=C(C(OCC)=O)N1.[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[C:24]([C:28]2[C:36]3[C:35](=[O:37])[NH:34][C:33]([C:38](OCC)=[O:39])=[N:32][C:31]=3[S:30][CH:29]=2)[CH:25]=[CH:26][CH:27]=1)=[O:21])[CH3:18].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=NC(CCCOC3C=C(CN)C=CN=3)=N2)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:86]2[CH:90]=[N:89][C:88]([O:91][CH2:92][CH2:93][O:94][C:95]3[CH:96]=[C:97]([CH2:101][NH2:102])[CH:98]=[CH:99][CH:100]=3)=[N:87]2)C=CC=CC=1>>[O:37]=[C:35]1[NH:34][C:33]([C:38](=[O:39])[NH:102][CH2:101][C:97]2[CH:98]=[CH:99][CH:100]=[C:95]([O:94][CH2:93][CH2:92][O:91][C:88]3[N:89]=[CH:90][NH:86][N:87]=3)[CH:96]=2)=[N:32][C:31]2[S:30][CH:29]=[C:28]([C:24]3[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=3)[C:20]([O:19][CH2:17][CH3:18])=[O:21])[C:36]1=2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,624,152 | [Pd+2] | Cl | [OH-] | null | ord_dataset-35c51552812941cda45194a013d34bb9 | 2015-01-01T00:08:00 | true | To a solution of (6R)-8-benzyl-6-(methoxymethyl)-N-methyl-N-(1-methylpropyl)-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepin-3-amine (297 mg) in methanol (10 mL) was added 20% Pd(OH)2/C (40 mg), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 4 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To a solution of the obtained crude product in ethyl acetate (10 mL) was added a 4 N hydrogen chloride-ethyl acetate solution (220 μL), and the mixture was stirred for 1 hr. The reaction mixture was filtered, and the obtained crystals were washed with ethyl acetate to give the title compound (141 mg, 55%). | CCC(C)N(C)c1cnc2c(n1)O[C@@H](COC)CNC2 | null | CCC(C)N(C)c1cnc2c(n1)O[C@@H](COC)CN(Cc1ccccc1)C2 | null | null | C([N:8]1[CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH3:24])[CH:20]([CH3:23])[CH2:21][CH3:22])=[N:18][C:12]=2[O:11][C@@H:10]([CH2:25][O:26][CH3:27])[CH2:9]1)C1C=CC=CC=1.C(OCC)(=O)C.[ClH:34]>CO.[OH-].[OH-].[Pd+2]>[ClH:34].[CH3:27][O:26][CH2:25][C@H:10]1[CH2:9][NH:8][CH2:14][C:13]2[N:15]=[CH:16][C:17]([N:19]([CH3:24])[CH:20]([CH3:23])[CH2:21][CH3:22])=[N:18][C:12]=2[O:11]1 | 4 | CO | CCOC(C)=O | null | 50 | null | 55 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
115,567 | [K+] | null | null | null | ord_dataset-d182ca8cf3f34de69c7a38343db8c930 | 1984-01-01T00:03:00 | true | A mixture of 2-mercapto-4-(4-methoxyphenyl)-5-(4-chlorophenyl)pyrimidine* (7 g) and potassium carbonate (8 g) in 200 ml acetone was treated with methyl iodide (4.8 ml) and stirred 5 hours at room temperature. The reaction mixture was filtered and concentrated on the rotary evaporator. Chromatography on silica gel and crystallization from ethanol gave the title compound (3.4 g), m.p. 127°-130°. Infrared and H-NMR spectra were consistent with the assigned structure. MS 342 (M+). | COc1ccc(-c2nc(SC)ncc2-c2ccc(Cl)cc2)cc1 | null | O=C([O-])[O-] | COc1ccc(-c2nc(S)ncc2-c2ccc(Cl)cc2)cc1 | null | [SH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:5]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:4][N:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:23][S:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:5]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:4][N:3]=1 | 5 | CC(C)=O | CI | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,324,118 | C[O+](C)C | F[B-](F)(F)F | null | null | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | 2013-01-01T00:08:00 | true | 4-[(3-Chloro-2-methylphenyl)carbonyl]-2-piperazinone (I131)(250 mg, 0.989 mmol) was suspended in dry Dichloromethane (DCM) (3 mL) before treating with trimethyloxonium tetrafluoroborate (185 mg, 1.187 mmol) and stirring for 16 hours at RT under argon before adding 5-methyl-1,3-thiazole-4-carbohydrazide (I123) (233 mg, 1.484 mmol) and stirring for a further 3 hours. DCM was removed by evaporation and the residue was dissolved in 1-butanol (3.00 mL) before heating at 110° C. for 4 hours then cooled to RT overnight. The reaction was worked up by diluting with DCM (50 ml) and washing with saturated sodium bicarbonate solution (50 ml). The aqueous layer was extracted with DCM (2×30 ml), the combined extracts were washed with brine (30 ml), dried (MgSO4), filtered and evaporated to afford a pale yellow cloudy gum as crude product. The product was purified on 50 g Isolera column, eluting with DCM (3CV) then 0-10% MeOH/DCM over 10CV. The desired fractions were isolated, the solvent evaporated and the residue was further purified by MDAP (formic acid method). The desired fraction was identified and the solvent evaporated to afford a white foam of desired product in 130 mg. | Cc1scnc1-c1nnc2n1CCN(C(=O)c1cccc(Cl)c1C)C2 | null | Cc1c(Cl)cccc1C(=O)N1CCNC(=O)C1 | Cc1scnc1C(=O)NN | null | [Cl:1][C:2]1[C:3]([CH3:17])=[C:4]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][C:12](=O)[CH2:11]2)=[O:9])[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.C[O+](C)C.[CH3:27][C:28]1[S:32][CH:31]=[N:30][C:29]=1[C:33]([NH:35][NH2:36])=O>ClCCl>[Cl:1][C:2]1[C:3]([CH3:17])=[C:4]([C:8]([N:10]2[CH2:15][CH2:14][N:13]3[C:33]([C:29]4[N:30]=[CH:31][S:32][C:28]=4[CH3:27])=[N:35][N:36]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:6][CH:7]=1 | 16 | ClCCl | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,446,304 | O=C([O-])O | O=C(n1ccnc1)n1ccnc1 | [Na+] | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | 6-chloro-N2-methylpyridine-2,3-diamine (1-2) (35 g, 222 mmol) and 1,1′-Carbonyldiimidazole (63 g, 389 mmol) were added to a round bottom flask and suspended in DMF (150 mL). The solution was heated to 80° C. in an oil bath overnight. The reaction was then suspended in ethyl acetate and sodium bicarbonate. The suspension was washed with sodium bicarbonate, brine (×5), dried over sodium sulfate, filtered, and concentrated to produce the solid 5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-3). MS (M+H)+: observed=184.2, calculated=184.6. | Cn1c(=O)[nH]c2ccc(Cl)nc21 | null | CNc1nc(Cl)ccc1N | CN(C)C=O | null | [Cl:1][C:2]1[N:7]=C(NC)[C:5]([NH2:10])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][N:24]([CH:26]=[O:27])[CH3:25]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[C:23]2[N:24]([CH3:25])[C:26](=[O:27])[NH:10][C:5]2=[CH:4][CH:3]=1 | null | CCOC(C)=O | null | null | 80 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
70,112 | O=P(O)(O)O | null | null | null | ord_dataset-06d4002fc4d34860a0688cba690e12dc | 1980-01-01T00:09:00 | true | A solution of 46 grams (0.17 mol) of 3-chloro-1-methyl-7-benzoylindole in 250 ml of methoxy-ethanol and 60 ml of 70% phosphoric acid was heated at reflux under a nitrogen atmosphere for 5 hours. The solution was then cooled and diluted with 1.5 liters of water. The organic materials were extracted with methylene chloride and concentrated. The concentrated extract was chromatographed on silica gel and the product eluted with isopropyl ether. The residue obtained crystallized upon standing and was recrystallized from isopropyl alcohol to give 8.9 grams of 1-methyl-7-benzoylindolin-2-one, having a m.p. of 89°-90.5° C. | CN1C(=O)Cc2cccc(C(=O)c3ccccc3)c21 | null | Cn1cc(Cl)c2cccc(C(=O)c3ccccc3)c21 | COC(C)O | null | Cl[C:2]1[C:10]2[C:5](=[C:6]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:19])[CH:3]=1.C[O:21]C(O)C>P(=O)(O)(O)O.O>[CH3:19][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:2][C:3]1=[O:21] | null | O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,325,376 | null | null | null | null | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | 2013-01-01T00:08:00 | true | This compound was prepared from tert-butyl 3-(1H-indazol-5-yl)azetidine-1-carboxylate and 4-fluoro-3-(oxazol-4-yl)benzene-1-sulfonyl chloride by analogy to the method outlined in example 44.c, below). | CC(C)(C)OC(=O)N1CC(c2ccc3c(cnn3S(=O)(=O)c3ccc(F)c(-c4cocn4)c3)c2)C1 | null | O=S(=O)(Cl)c1ccc(F)c(-c2cocn2)c1 | CC(C)(C)OC(=O)N1CC(c2ccc3[nH]ncc3c2)C1 | null | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][C:23]=1[C:32]1[N:33]=[CH:34][O:35][CH:36]=1>>[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]4[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]4)=[CH:7][CH:8]=3)[CH:3]=[N:2]2)(=[O:30])=[O:29])=[CH:24][C:23]=1[C:32]1[N:33]=[CH:34][O:35][CH:36]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,278,481 | CC(C)[Mg]Cl | null | null | null | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | 2013-01-01T00:04:00 | true | To a solution of aminopyrazine (3.85 g, 40.5 mmol) in THF (120 mL) was added isopropylmagnesium chloride (2.0 M THF solution, 19 mL, 38 mmol) dropwise at 0° C. The resulting slurry was stirred at room temperature for 30 min. A solution of commercially available (2S,4R)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate (3.2 g, 12.9 mmol) in THF (10 mL) was added to the slurry. The reaction mixture was stirred at room temperature for 4 h and quenched with methanol (3 mL). After concentration in vacuo, ethyl acetate (120 mL) and 1N HCl (60 mL) were added to the residue. The organic layers were washed with 1N HCl, water, brine, and dried over Na2SO4, and filtered. Concentration gave (2S,4R)-tert-butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 65A (4.1 g, 100%) as a colorless foam. LC/MS [M+H]+: 311; Ret time (Method F): 1.46 min. | CC(C)(C)OC(=O)N1C[C@H](F)C[C@H]1C(=O)Nc1cnccn1 | null | Nc1cnccn1 | COC(=O)[C@@H]1C[C@@H](F)CN1C(=O)OC(C)(C)C | null | [NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[F:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26](OC)=[O:27])[CH2:15]1>C1COCC1>[F:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@H:16]([C:26](=[O:27])[NH:1][C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:15]1 | 0.5 | C1CCOC1 | null | null | 25 | null | 102.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
702,025 | null | null | null | null | ord_dataset-bbd7e53f000345838ad4920a07a169ff | 2006-01-01T00:03:00 | true | Prepared from (2′-fluoro-3-{3-[3-(2-methoxymethylsulfanyl-imidazol-1-yl)-phenyl]-3-oxo-propionylamino}-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example K71) by treatment with TFA in CH2Cl2 according to the general procedure M. Obtained as a light yellow solid (100 mg). | COCSc1nccn1-c1cccc(C2=Nc3ccc(-c4ccccc4F)cc3NC(=O)C2)c1 | null | COCSc1nccn1-c1cccc(C(=O)CC(=O)Nc2cc(-c3ccccc3F)ccc2NC(=O)OC(C)(C)C)c1 | null | null | C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[CH:10][C:9]=1[NH:21][C:22](=[O:41])[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]2[CH:36]=[CH:35][N:34]=[C:33]2[S:37][CH2:38][O:39][CH3:40])[CH:27]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N:32]4[CH:36]=[CH:35][N:34]=[C:33]4[S:37][CH2:38][O:39][CH3:40])[CH:27]=3)[CH2:23][C:22](=[O:41])[NH:21][C:9]=2[CH:10]=1 | null | O=C(O)C(F)(F)F | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,460,441 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (211 mg, 1 mmol), 6-chloro-4-methoxypyridin-3-amine (150 mg, 0.95 mmol) and para-toluenesulphonic acid (190 mg, 1 mmol) in 1,4-dioxane (2 mL) was heated at 100° C. for 1 h. The mixture was cooled and filtered, the solid was washed with dioxane and dried in vacuo to give the product as a cream coloured solid (436 mg, >100%). 1H NMR (400 MHz, DMSO): δ 9.82 (s, 1H); 8.76 (s, 1H); 8.44 (s, 2H); 7.38 (s, 1H); 4.00 (s, 3H); 2.99-2.92 (m, 3H). | CNc1nc(Nc2cnc(Cl)cc2OC)ncc1C(F)(F)F | null | COc1cc(Cl)ncc1N | CNc1nc(Cl)ncc1C(F)(F)F | null | Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:22][CH3:23])[CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=2)=[C:17]([O:22][CH3:23])[CH:16]=1 | null | C1COCCO1 | null | null | 100 | null | 137.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
520,294 | [Al+3] | [H-] | [Li+] | null | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | 2001-01-01T00:10:00 | true | Prepared according to the method described in Example 1b) from lithium aluminium hydride (41.9 ml, 1.0M solution in ether) and solution (2S)-2-(biphenyl-4-yloxy)propanoic acid, ethyl ester (11.3 g, Example 2a)) in dry tetrahydrofuran (200 ml) at 0° C. The sub-title compound obtained after work-up was used directly without further purification (9.52 g). | C[C@@H](CO)Oc1ccc(-c2ccccc2)cc1 | null | CCOC(=O)[C@H](C)Oc1ccc(-c2ccccc2)cc1 | null | null | [H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[CH:11][C:10]([O:13][C@@H:14]([CH3:20])[C:15](OCC)=[O:16])=[CH:9][CH:8]=1>O1CCCC1>[C:7]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:8]=[CH:9][C:10]([O:13][C@@H:14]([CH3:20])[CH2:15][OH:16])=[CH:11][CH:12]=1 | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
151,738 | [H-] | [Na+] | null | null | ord_dataset-772de90433b44abbbacf9b316b845c31 | 1986-01-01T00:12:00 | true | In a 200 ml round-bottom flask is placed a solution of 8.0 g of p-(1-imidazolylmethyl)aniline prepared as described in Reference Example 3, and 30 ml of formic acid in 80 ml of toluene. The flask was fitted with a water separator, and the solution was refluxed for 4 hours. After concentration under reduced pressure, the residual solid was recrystallized from ethanol-diethyl ether to give 6.4 g of p-(1-imidazolylmethyl)-N-formylaniline as colorless prisms. M.P.: 121°-123° C. To a suspension of 0.48 g of 50% sodium hydride in 50 ml of dry dimethylformamide was added 2.01 g of the formylaniline and mixture was heated to 100° C. A solution of 1.81 g of ethyl α-bromopropionate in 30 ml of dry dimethylformamide was added to the mixture and the reaction mixture was heated at 100° C. for 16 hours. After removal of the solvent under reduced pressure, 50 ml of dichloromethane was added to the residue, and the solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel using dichloromethane-ethanol (20:1 by volume) to give 1.58 g of N-formyl-N-[p-(1-imidazolylmethyl)phenyl]alanine ethyl ester as a pale brown oil. Then, a solution of 1.58 g of the resulting ester and 5 ml of concentrated hydrochloric acid in 50 ml of ethanol was stirred for 40 hours at room temperature. After concentration under reduced pressure, the residual solid was recrystallized from ethanol-diethyl ether to give 1.18 g of N-[p-(1-imidazolylmethyl)phenyl]alanine ethyl ester dihydrochloride as pale yellow crystals. M.P.: 154°-159° C. | CCOC(=O)[C@H](C)N(C=O)c1ccc(Cc2ncc[nH]2)cc1 | null | CCOC(=O)C(C)Br | O=CNc1ccc(Cc2ncc[nH]2)cc1 | null | [H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][C:9]1[CH:17]=[CH:16][C:12]([NH:13][CH:14]=[O:15])=[CH:11][CH:10]=1.Br[CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[CH2:23]([O:22][C:20](=[O:21])[C@H:19]([CH3:25])[N:13]([CH:14]=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C:4]2[NH:3][CH:7]=[CH:6][N:5]=2)=[CH:17][CH:16]=1)[CH3:24] | null | CN(C)C=O | null | null | 100 | 52.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
92,487 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-dba7c8cf38834984ba5e6376158f46fe | 1982-01-01T00:03:00 | true | Ethyl 5-ethylthiazol-2-ylcarbamoylcarboxylate (685 mg., 3 mmoles), 1 N potassium carbonate (3 ml., 3 equivalents), water (22 ml.) and ethanol (2--3 ml.) were heated on a steam bath. After 10 minutes, dissolution was nearly complete. After an additional 15 minutes, tlc (chloroform-5% acetic acid) indicated reaction was complete. The cooled reaction mixture was filtered, and crude product (380 mg.) precipitated from the filtrate by acidification with acetic acid. Recrystallization of the crude from isopropyl alcohol gave purified 5-ethylthiazol-2-ylcarbamoylcarboxylic acid [280 mg., m.p. 206.5° C. (dec)]. | CCc1cnc(NC(=O)C(=O)O)s1 | null | CCOC(=O)C(=O)Nc1ncc(CC)s1 | null | null | [CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]([O:13]CC)=[O:12])=[O:10])=[N:5][CH:4]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].O.C(O)C>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[S:7][C:6]([NH:8][C:9]([C:11]([OH:13])=[O:12])=[O:10])=[N:5][CH:4]=1)[CH3:2] | 0.17 | ClC(Cl)Cl | CCO | O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
528,456 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | ord_dataset-f027aa93238e424fbbf9bad1c7699adc | 2001-01-01T00:12:00 | true | 2-Tert-butyldimethylsilyl-1-dimethylsulfamoyl imidazole (1) (4.1 g, 14.2 mmol) is taken up in 47 mL of anhydrous THF and cooled to −200° C. n-BuLi (8.9 mL, 14.2 mmol) is added dropwise to the solution of (1). The resultant solution is stirred at −20° C. for 45 min. Cyclohexylmethyl iodide (2) (3.14 g, 14 mmol) is then added dropwise to the reaction mixture. Then reaction is warmed to rt and stirred overnight. The next day the reaction is quenched with saturated ammonium chloride and diluted with water. The mixture is extracted with ethyl acetate (3×100 mL). The organic layers are combined and washed with water followed by brine. The organic phase is dried over sodium sulfate and the solvent removed under reduced pressure. Flash chromatography (4:1 ethyl acetate/hexane) affords 2.26 g (5.6 mmol) of 5-cyclohexylmethyl-2-tert-butyldimethylsilyl-1-dimethylsulfamoyl imidazole (3). (3) (2.26 g, 5.6 mmol) is taken up in 56 mL of THF and cooled to 0° C. A 1M solution of TBAF in THF (5.6 mL, 5.6 mmol) is added dropwise to the solution of (3). The reaction is warmed to rt and stirred overnight. The next day the reaction is quenched with water and then extracted with ethyl acetate. The organic layer is washed with water followed by brine. The organic phase is dried over sodium sulfate and the solvent removed under reduced pressure. Flash chromatography (1:1 ethyl acetate/hexane) affords 1.2 g (4.42 mmol) of 5-cyclohexylmethyl-1-dimethylsulfamoyl imidazole (4). (4) (1.2 g, 4.42 mmol) is taken up in 25 mL of a 1.5N HCl solution and heated at reflux for 2 h. The reaction is cool to rt and diluted with ethyl acetate. The mixture is brought to pH 13 with 2N NaOH and then extracted with chloroform (4×100 mL). The organic layers are combined and washed with water followed by brine. The organic phase is dried over sodium sulfate and the solvent removed under reduced pressure. Flash chromatography (9:1 chloroform/methanol) affords 700 mg (4.27 mmol) of 4(5)-cyclohexylmethyl-1H-imidazole (5) (J-1). | CN(C)S(=O)(=O)n1cncc1CC1CCCCC1 | null | CN(C)S(=O)(=O)n1c(CC2CCCCC2)cnc1[Si](C)(C)C(C)(C)C | null | null | [CH:1]1([CH2:7][C:8]2[N:12]([S:13](=[O:18])(=[O:17])[N:14]([CH3:16])[CH3:15])[C:11]([Si](C(C)(C)C)(C)C)=[N:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH:1]1([CH2:7][C:8]2[N:12]([S:13](=[O:18])(=[O:17])[N:14]([CH3:15])[CH3:16])[CH:11]=[N:10][CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1 | 8 | CCCCCC | CCOC(C)=O | C1CCOC1 | 0 | 78.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
637,204 | [Pd] | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | c1coc(P(c2ccco2)c2ccco2)c1 | null | ord_dataset-a192df1b44174b5886ef2005f759d553 | 2004-01-01T00:05:00 | true | To a stirred solution of 100 mg (0.27 mmol) (7-iodo-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 3 ml dioxane were added 0.2 g (0.54 mmol) tri-n-butyl-(1-cyclohex-1-enyl)-stannane, 5.0 mg (0.009 mmol) bis(dibenzylideneacetone)palladium and 10 mg (0.043 mmol) trifurylphosphine. The mixture was heated at 100° C. for 16 h and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1:4) afforded 16 mg (7-Cyclohex-1-enyl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester (18%) as an off white solid; F.p.: 164-173° C. | COC(=O)Nc1nc2c(OC)ccc(C3=CCCCC3)c2s1 | null | CCCC[Sn](CCCC)(CCCC)C1=CCCCC1 | COC(=O)Nc1nc2c(OC)ccc(I)c2s1 | null | [CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13](I)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.C([Sn](CCCC)(CCCC)[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1)CCC.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1 | null | C1COCCO1 | null | null | 100 | 18.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,315,454 | [Fe] | [Na+] | [OH-] | null | ord_dataset-2d6edb8ffd434003bb508360153bd9bb | 2013-01-01T00:07:00 | true | Iron powder (0.15 g, 2.574 mmol) was added to a solution of dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine (200 mg, 0.86 mmol) in acetic acid (3 ml) and stirred overnight at room temperature. The reaction mixture was poured into ice water and basified with dilute sodium hydroxide solution and then filtered. The filtrate was extracted with ethyl acetate, and the organic layer was washed with water, then brine and dried. Evaporation to dryness gave N1,N1-dimethyl-2-oxazol-2-yl-benzene-1,4-diamine (150 mg, 88.2%) as oil. | CN(C)c1ccc(N)cc1-c1ncco1 | null | CN(C)c1ccc([N+](=O)[O-])cc1-c1ncco1 | null | null | [CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]1[O:13][CH:14]=[CH:15][N:16]=1.[OH-].[Na+]>C(O)(=O)C.[Fe]>[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]1[O:13][CH:14]=[CH:15][N:16]=1 | 8 | CC(=O)O | null | null | 25 | 85.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
198,349 | null | null | null | null | ord_dataset-f6fafbb8ce5f4ef099be3a772075ec97 | 1989-01-01T00:10:00 | true | N-Bromosuccinimide (1.3 g, 7.3 mmol) is added to a suspension of 9-(4-chlorophenyl)methylguanine (1.5 g; 5.4 mmol), Example 3, in glacial acetic acid (100 ml) and the mixture is stirred for 20 hours at room temperature. The solution is poured into water (400 ml) and the resulting precipitate is filtered, washed with water and methanol and dried. Yield: 1.0 g; mp>300° C. | Nc1nc2c(nc(Br)n2Cc2ccc(Cl)cc2)c(=O)[nH]1 | null | O=C1CCC(=O)N1Br | Nc1nc2c(ncn2Cc2ccc(Cl)cc2)c(=O)[nH]1 | null | [Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH:25]=[N:24][C:23]3[C:22](=[O:26])[NH:21][C:20]([NH2:27])=[N:19][C:18]2=3)=[CH:12][CH:11]=1.O>C(O)(=O)C>[Br:1][C:25]1[N:17]([CH2:16][C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[C:18]2[N:19]=[C:20]([NH2:27])[NH:21][C:22](=[O:26])[C:23]=2[N:24]=1 | 20 | CC(=O)O | O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,023,791 | CN1CCNCC1 | null | null | null | ord_dataset-136cfada6ce247b4919085a57363459e | 2011-01-01T00:01:00 | true | The title compound was prepared following the procedure described in the synthesis of 28a using 27d and 1-methylpiperazine. 1H-NMR (DMSO-d6) δ (ppm): 2.28 (3H, s), 2.64 (4H, brm), 3.22 (4H, brm), 7.21 (1H, m), 7.58 (1H, m), 7.79 (3H, m), 8.67 (1H, m). m/z 384.2 | CN1CCN(c2cc3[nH]cc4c(=O)n(-c5ccsc5)nc-4c3cc2F)CC1 | null | O=c1c2c[nH]c3cc(F)c(F)cc3c-2nn1-c1ccsc1 | O=c1c2c[nH]c3cc(N4CCNCC4)c(F)cc3c-2nn1-c1ccccc1 | null | FC1[C:11]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=CC2NC=C3C(=O)N(C4C=CC=CC=4)N=C3C=2C=1.F[C:29]1[C:30]([F:48])=[CH:31][C:32]2[C:33]3[C:34]([C:39](=[O:47])[N:40]([C:42]4[CH:46]=[CH:45][S:44][CH:43]=4)[N:41]=3)=[CH:35][NH:36][C:37]=2[CH:38]=1.CN1CCNCC1>>[F:48][C:30]1[C:29]([N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[CH:38][C:37]2[NH:36][CH:35]=[C:34]3[C:39](=[O:47])[N:40]([C:42]4[CH:46]=[CH:45][S:44][CH:43]=4)[N:41]=[C:33]3[C:32]=2[CH:31]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
849,553 | [K+] | null | null | null | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | 2008-01-01T00:11:00 | true | 3,4-Dihydroxy-benzaldehyde (2.1 g, 0.015 mol), K2CO3 (4.0 g, 0.03 mol) and 1-iodohexane (6.4 g, 0.03 mol) were stirred in 100 ml of 1-butanol under reflux for 24 h. After cooling, the 1-butanol was removed by rotary evaporation. The residue was dissolved in 200 ml of ether, washed with water (dist.) and brine. The solution was dried over Na2SO4 and the solvent was removed to yield 3.7 g 3,4-Bis-hexyloxy-benzaldehyde (85%) as a dark solid. 1H NMR (400 MHz, CDCl3): δ 9.83 (s, 1H), 7.41 (m, 2H), 6.95 (d, 1H, J=8.5 Hz), 4.07 (m, 4H), 1.85 (m, 4H), 1.48 (m, 4H), 1.35 (m, 8H), 0.91 (m, 6H). | CCCCCCOc1ccc(C=O)cc1OCCCCCC | null | O=Cc1ccc(O)c(O)c1 | CCCCCCI | O=C([O-])[O-] | [OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[CH:5]=[O:6].[C:11]([O-:14])([O-])=O.[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(O)CCC>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:14][CH2:11][CH2:8][CH2:9][CH2:2][CH2:3][CH3:4])[CH:5]=[O:6])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23] | null | CCCCO | null | null | null | 161 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,390,937 | null | null | null | null | ord_dataset-31641fb65b34430fa7435229b949b604 | 2014-01-01T00:01:00 | true | The title compound was prepared in the same manner as described in example 21 from 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (23 mg, 0.062 mmol), ethanol (0.7 mL), and dimethylamine (0.461 mL, 0.923 mmol). The product was dried in vacuum oven at 50° C. for 5 hr and collected as 0.016 g (67%). LCMS E-S (M+H)=383.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44 (d, J=6.57 Hz, 6H), 2.05-2.25 (m, 6H), 3.14 (s, 6H), 4.34 (d, J=4.80 Hz, 2H), 4.99 (dt, J=13.39, 6.69 Hz, 1H), 5.89 (s, 1H), 6.94 (s, 1H), 7.96 (s, 1H), 8.64 (t, J=4.93 Hz, 1H), 11.56 (br. s., 1H). | Cc1cc(C)c(CNC(=O)c2cc(N(C)C)nc3c2cnn3C(C)C)c(=O)[nH]1 | null | Cc1cc(C)c(CNC(=O)c2cc(Cl)nc3c2cnn3C(C)C)c(=O)[nH]1 | CNC | null | Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[CH3:27][NH:28][CH3:29]>C(O)C>[CH3:27][N:28]([CH3:29])[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1 | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
256,576 | BrCc1ccc(-c2ccccc2-c2nnn(C(c3ccccc3)(c3ccccc3)c3ccccc3)n2)cc1 | null | null | null | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | 1992-01-01T00:10:00 | true | Substituting ethyl butyrylacetate for ethyl 3-oxooctanoate and 4-bromobenzyl bromide for 4-bromomethyl-2'-(2-(triphenylmethyl)tetrazol-5-yl)-biphenyl in Example 4 gave the title compound. | CCCC(=O)C(Cc1ccc(Br)cc1)C(=O)OCC | null | BrCc1ccc(Br)cc1 | CCCCCC(=O)CC(=O)OCC | null | [O:1]=[C:2]([CH2:9][CH2:10][CH2:11]CC)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.BrCC1C=CC(C2C=CC=CC=2C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=CC=1>>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][CH:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:17][CH:16]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
621,675 | O=S(=O)(O)O | [Na+] | [OH-] | null | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | 2004-01-01T00:01:00 | true | A mixture of 5-bromo-2-(1-hydroxy-1-methylethyl) pyridine N-oxide from step 2 of example 30 (1.29 g) and 25% aqueous sulfuric acid was heated at 130° C. for 2 days. After cooling, the mixture was made slightly basic using ION aqueous sodium hydroxide and partitioned between ethyl acetate and water. The crude product from evaporation of the organic phase was used as such in step 2. | C=C(C)c1ccc(Br)c[n+]1[O-] | null | CC(C)(O)c1ccc(Br)c[n+]1[O-] | null | null | [Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](O)([CH3:11])[CH3:10])=[N+:6]([O-:8])[CH:7]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:11])=[CH2:10])=[N+:6]([O-:8])[CH:7]=1 | null | null | null | null | 130 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
554,869 | null | null | null | null | ord_dataset-ec9decb576c4424c9685993f6262bd9c | 2002-01-01T00:07:00 | true | The procedures of Example 1-(1) were followed, except for replacing the ethyl isocyanoacetate with 9.9 g (0.1 mol) of methyl isocyanoacetate, to obtain 15.4 g (0.055 mol 61.5% based on the 2-methoxy-4-nitrobenzoic acid) of the title compound. | COC(=O)c1ncoc1-c1ccc([N+](=O)[O-])cc1OC | null | COc1cc([N+](=O)[O-])ccc1C(=O)O | [C-]#[N+]CC(=O)OC | null | [N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13]>>[CH3:8][O:9][C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:11]=1[C:12]1[O:13][CH:2]=[N:1][C:3]=1[C:4]([O:6][CH3:7])=[O:5] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
678,753 | Cl | null | null | null | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | 2005-01-01T00:07:00 | true | 2 mL of an 6 N aqueous solution of hydrochloride were added to the mixture of tert-butyl N-(3-{3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanyl}-3-oxopropyl)-N-(2-hydroxyethyl)carbamate (0.040 g, 0.000070 mol). in acetone (5 mL). The mixture was stirred at 45° C. for 1.5 hours. The solvent was removed under removed pressure. Water (10 mL) was added to the residue, the mixture was lyophilized. The residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min) to yield 1-{3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanyl}-3-[(2-hydroxyethyl)amino]-1-propanone (0.003 g, 0.00001 mol). | Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)nn2C1CN(C(=O)CCNCCO)C1 | null | CC(C)(C)OC(=O)N(CCO)CCC(=O)N1CC(n2nc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1 | null | null | Cl.[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:25]3[CH2:28][N:27]([C:29](=[O:43])[CH2:30][CH2:31][N:32]([CH2:40][CH2:41][OH:42])C(=O)OC(C)(C)C)[CH2:26]3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:4]=12>CC(C)=O>[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:25]3[CH2:26][N:27]([C:29](=[O:43])[CH2:30][CH2:31][NH:32][CH2:40][CH2:41][OH:42])[CH2:28]3)[N:10]=[C:11]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:16][CH:17]=3)[C:4]=12 | 1.5 | CC(C)=O | null | null | 45 | null | 14.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,677,953 | [K+] | null | null | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | To the stirred solution of (R)-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (5.0 g, 26.3 mmol), K2CO3 (10.90 g, 79 mmol) and methyl iodide (6.58 ml, 105 mmol) was added in DMF (50 mL) and stirred for overnight at 25° C. Water was added (130 mL) and extracted with ethyl acetate (2×30 mL). The organic phase was washed with aq. Sodium bicarbonate solution (2×20 mL), dried over Na2SO4 and filtered. The clear organic phase was evaporated in vacuo to get title compound (4.5 g) m/z 204.09. | COC(=O)[C@H]1CC(=O)c2ccccc2C1 | null | O=C([O-])[O-] | O=C1C[C@H](C(=O)O)Cc2ccccc21 | null | [O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([OH:14])=[O:13])[CH2:3]1.[C:15]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3]1 | 8 | CN(C)C=O | O | CI | 25 | null | 83.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
172,489 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-7860c6f563014da8948ede63b7110bde | 1988-01-01T00:05:00 | true | 73 parts by weight of potassium 3-cresolate, 107 parts by weight of 3,4-dichlorobenzotrifluoride and 6.9 parts by weight of potassium carbonate in 500 parts by volume of dimethylsulfoxide were stirred at 140° C. for 8 hours. The reaction mixture was cooled to room temperature and was poured into 2,000 parts by volume of water. The oily residue was taken up in ether, and the organic phase was dried with magnesium sulfate, filtered, and concentrated under reduced pressure. Fractional distillation gave 120 parts by weight (84% of theory) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-toluene of boiling point 91°-96° C./0.1 bar and refractive index nD25 : 1.5268. | Cc1cccc(Oc2ccc(C(F)(F)F)cc2Cl)c1 | null | FC(F)(F)c1ccc(Cl)c(Cl)c1 | Cc1cccc(O)c1C(=O)[O-] | null | [C:1]1(C([O-])=O)[C:2]([CH3:8])=[CH:3][CH:4]=[CH:5][C:6]=1[OH:7].[K+].[Cl:13][C:14]1[CH:15]=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:17]=[CH:18][C:19]=1Cl.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>CCOCC.O>[Cl:13][C:14]1[CH:15]=[C:16]([C:21]([F:22])([F:23])[F:24])[CH:17]=[CH:18][C:19]=1[O:7][C:6]1[CH:1]=[C:2]([CH3:8])[CH:3]=[CH:4][CH:5]=1 | null | CS(C)=O | CCOCC | O | 25 | null | 84 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
840,304 | null | null | null | null | ord_dataset-074f86301ec5441ab3b52d902ac06949 | 2008-01-01T00:09:00 | true | To a solution of [6-(2-cyano-vinyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-carbamic acid tert-butyl ester (2.7 g, 9.05 mmol) in DCM (40 mL) was added TFA (15 mL). The resulting mixture was stirred at RT for 1 h. Solvent was removed. The residue was redissolved in EtOAc. The organic layer was washed with sat. NaHCO3, H2O, brine, dried over MgSO4 and removed solvent. The crude product was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH (2M NH3) mixture (97:3) gave final compound (1.6 g, 89%). MS m/z: 199.3 (M+H). Calc'd. for C13H14N2-198.26. | N#CC=Cc1ccc2c(c1)CCCC2N | null | CC(C)(C)OC(=O)NC1CCCc2cc(C=CC#N)ccc21 | null | null | C(OC(=O)[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[CH:19][C:20]#[N:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]#[N:21])[CH:15]=[CH:16][C:17]1=2 | 1 | ClCCl | O=C(O)C(F)(F)F | null | 25 | null | 89.2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
28,365 | O=C(n1ccnc1)n1ccnc1 | null | null | null | ord_dataset-2cb52357eb5f43c2be56ad5c0662f18f | 1977-01-01T00:08:00 | true | To a solution of 360 mg. of 1,1'-carbonyldiimidazole in 6 ml. of dry tetrahydrofuran at 140° C. is added dropwise 500 mg. of 3-carboxy-4-oxo-4H-pyrimido[2,1-b]benzothiazole in 6 ml. of dry dimethylformamide. After heating for 3 hrs., 186 mg. of 5-aminotetrazole is added, and the heating maintained for an additional 15 min. The reaction mixture is cooled and the precipitated product filtered. Recrystallization from dimethylformamide gives 200 mg. of the desired product, m.p. 330°-332° C. | O=C(Nc1nnn[nH]1)c1cnc2sc3ccccc3n2c1=O | null | Nc1nnn[nH]1 | O=C(O)c1cnc2sc3ccccc3n2c1=O | null | C(N1C=CN=C1)(N1C=CN=C1)=O.O1CCCC1.[C:18]([C:21]1[C:29](=[O:30])[N:28]2[C:24]([S:25][C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=32)=[N:23][CH:22]=1)([OH:20])=O.[NH2:35][C:36]1[NH:40][N:39]=[N:38][N:37]=1>CN(C)C=O>[NH:37]1[C:36]([NH:35][C:18]([C:21]2[C:29](=[O:30])[N:28]3[C:24]([S:25][C:26]4[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=43)=[N:23][CH:22]=2)=[O:20])=[N:40][N:39]=[N:38]1 | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
894,998 | null | null | null | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | A mixture of 0.112 g (0.252 mmol) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4,5-dimethyl-benzamide and 0.069 mL (0.756 mmol) of methyl propiolate was stirred in 0.5 mL of DMA at 110° C. overnight. The vial was cooled to room temperature, and the contents were poured into stirring water. The precipitate was collected and chromatographed (10-60% EtOAc in hexanes). Fractions containing predominantly the major product were collected and further purified by precipitating from dichloromethane with hexanes to provide 57 mg of a white powder. The filtrate was combined with the mixed fractions from the first chromatography, and the resulting mixture was chromatographed again to provide 22 mg of the title compound as a pale yellow solid for a total yield of 79 mg (0.149 mmol; 59%), mp: 199° C. ESI MS (m/z 528, 100, M−H). | COC(=O)c1cn(-c2cc(C(=O)Nc3cc(C(C)(C)C)cc(NS(C)(=O)=O)c3OC)cc(C)c2C)nn1 | null | C#CC(=O)OC | COc1c(NC(=O)c2cc(C)c(C)c(N=[N+]=[N-])c2)cc(C(C)(C)C)cc1NS(C)(=O)=O | null | [N:1]([C:4]1[CH:5]=[C:6]([CH:27]=[C:28]([CH3:31])[C:29]=1[CH3:30])[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:11]=1[O:25][CH3:26])=[O:8])=[N+:2]=[N-:3].[C:32]([O:36][CH3:37])(=[O:35])[C:33]#[CH:34].O>CC(N(C)C)=O>[CH3:37][O:36][C:32]([C:33]1[N:3]=[N:2][N:1]([C:4]2[CH:5]=[C:6]([C:7](=[O:8])[NH:9][C:10]3[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[C:11]=3[O:25][CH3:26])[CH:27]=[C:28]([CH3:31])[C:29]=2[CH3:30])[CH:34]=1)=[O:35] | null | O | CC(=O)N(C)C | null | 25 | 42.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,545,951 | null | null | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | To a suspension of 6-((1H-benzo[d]imidazol-1-yl)methyl)-2-bromobenzo[d]thiazole from Step 1 of Example 1 (34.4 mg, 0.1 mmol) in DMA (3 mL) were added DIEA (15 mg, 0.12 mmol) and (1R,2R)-2-aminocyclohexanol (13.8 mg, 0.12 mmol) at rt. The reaction mixture was stirred in a sealed tube at 120° C. overnight. After cooling to rt, the mixture was concentrated under reduced pressure. The crude product was purified by preparative HPLC using a mixture of water (containing 5% CH3CN, 0.05% HCOOH) and CH3CN (containing 0.05% HCOOH) as the mobile phase and Varian Pursuit XRs C-18 column as the stationary phase to afford (1R,2R)-2-((6-((1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (22 mg, 58%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.99 (d, J=7.3 Hz, 1H), 7.60-7.72 (m, 2H), 7.55 (dd, J=2.6, 6.0 Hz, 1H), 7.26-7.34 (m, 1H), 7.12-7.25 (m, 3H), 5.47 (s, 2H), 4.76 (br s, 1H), 3.26-3.39 (m, 2H), 2.03 (d, J=10.0 Hz, 1H), 1.87 (d, J=9.4 Hz, 1H), 1.62 (d, J=4.7 Hz, 2H), 1.03-1.39 (m, 4H). LCMS (ESI) m/z 379 (M+H)+. | O[C@@H]1CCCC[C@H]1Nc1nc2ccc(Cn3cnc4ccccc43)cc2s1 | null | N[C@@H]1CCCC[C@H]1O | Brc1nc2ccc(Cn3cnc4ccccc43)cc2s1 | null | [N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]3[N:15]=[C:16](Br)[S:17][C:13]=3[CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.CCN(C(C)C)C(C)C.[NH2:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[OH:37]>CC(N(C)C)=O>[N:1]1([CH2:10][C:11]2[CH:20]=[CH:19][C:14]3[N:15]=[C:16]([NH:30][C@@H:31]4[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]4[OH:37])[S:17][C:13]=3[CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1 | 8 | CCN(C(C)C)C(C)C | CC(=O)N(C)C | null | 120 | null | 58.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,658,040 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | 2015-01-01T00:11:00 | true | A solution of 3-fluoro-4-hydroxy-5-methoxy-benzaldehyde (250 mg, 1.5 mmol) in DMF (2.5 mL) was treated with potassium carbonate (812 mg, 5.9 mmol) and stirred for 30 minutes. 2-Iodopropane (500 mg, 2.9 mmol) was added over 10 minutes and reaction mixture was stirred for 20 hours. The reaction mixture was partitioned between EtOAc and saturated aqueous sodium chloride solution. The organic layer was washed with saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate, filtered and concentrated in vacuo to give 3-fluoro-4-isopropoxy-5-methoxybenzaldehyde. To the aldehyde was added tert-butanol (6.7 mL) and 2-methylbut-2-ene (4 mL, 38.2 mmol) and the reaction mixture was cooled to 0° C. A solution of chlorite (345 mg, 3.8 mmol) and sodium dihydrogen phosphate hydrate (527 mg, 3.8 mmol) in water (6.7 mL) was added dropwise over 5 minutes, and the reaction mixture was stirred 30 minutes. The reaction mixture was warmed to room temperature and stirred for 12 hours. The reaction mixture was basified with 1 N NaOH solution and extracted with ethyl acetate (2×50 mL). The aqueous layer was acidified with 1 N HCl solution and extracted with EtOAc (4×50 mL). The combined organics were dried (Na2SO4), filtered, and concentrated in vacuo to afford 3-fluoro-4-isopropoxy-5-methoxy-benzoic acid (190 mg, 56%) as a white solid. ESI-MS m/z calc. 228.0. found 229.3 (M−1)+; Retention time: 1.57 minutes (3 min run). | COc1cc(C=O)cc(F)c1OC(C)C | null | CC(C)I | COc1cc(C=O)cc(F)c1O | null | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].I[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[O:10][CH:20]([CH3:22])[CH3:21])[CH:5]=[O:6] | 0.5 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
896,868 | null | null | null | null | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | 2009-01-01T00:08:00 | true | Similar procedure as described in example 273 was used, starting from (1-chloro-5,6-dimethoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine and 4-amino-benzonitrile to give 4-[3-(5-methyl-1H-pyrazol-3-ylamino)-5,6-dimethoxy-isoquinolin-1-ylamino]-benzonitrile. LC-MS m/e 401(MH+). | COc1ccc2c(Nc3ccc(C#N)cc3)nc(Nc3cc(C)[nH]n3)cc2c1OC | null | N#Cc1ccc(N)cc1 | COc1ccc2c(Cl)nc(Nc3cc(C)[nH]n3)cc2c1OC | null | Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:16][C:17]2[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=2)[N:3]=1.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1>>[CH3:22][C:20]1[NH:19][N:18]=[C:17]([NH:16][C:4]2[N:3]=[C:2]([NH:23][C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=3)[C:11]3[C:6]([CH:5]=2)=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[CH:21]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,438,508 | Cl | null | null | null | ord_dataset-275a3da8f45f4536ad29727f0ef9ba66 | 2014-01-01T00:06:00 | true | Methyl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate (224 mg, 0.89 mmol) and 37% HCl (813 μl, 26.7 mmol) were dissolved in dioxane (3 ml) and stirred under microwave irradiation at 100° C. for 6 hours. The solvents were evaporated and the residue was triturated with Et2O and sonicated. The solid was collected by suction filtration, washed with Et2O and dried under vacuum overnight to collect 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetic acid hydrochloride (230 mg, 94% yield). | O=C(O)C(c1cccc(F)c1)N1CCCCC1 | null | COC(=O)C(c1cccc(F)c1)N1CCCCC1 | null | null | [F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([O:11]C)=[O:10])[CH:5]=[CH:6][CH:7]=1.[ClH:19]>O1CCOCC1>[ClH:19].[F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1 | 6 | C1COCCO1 | null | null | 100 | null | 94.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
493,534 | [H-] | [Na+] | null | null | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | 2001-01-01T00:02:00 | true | Sodium hydride (60% suspension in oil, 1.2 g, 30.15 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (110 mL). Neat 3-methylpyrazole (2.47 g, 30.15 mmol) was added dropwise at 0° C. After the gas evolution subsided the cooling bath was removed and stirring was continued at room temperature. The [2-bromo-4-fluorophenyl]-(5,11-dihydro-pyrido [2,3-b][1,5]benzodiazepin-6-yl)-methanone of Step B (6 g, 18.07 mmol) was added in one portion to the clear solution. The mixture was placed in an oil bath (preheated at 130° C.) for 40 minutes, cooled and partitioned between water and ethyl acetate. The organic extracts were dried over magnesium sulfate and evaporated to dryness. The crude material was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with a hexane-ethyl acetate gradient (from 95:5 to 75:25) provided the less polar title compound (3.87 g) along with a mixture of 3- and 5-methylpyrazole regioisomers (0.860 g). The title compound (3.5 g, 51%) crystallized by sonication from hexane-ethanol, m.p. 208-209° C. (dec). | Cc1ccn(-c2ccc(C(=O)N3Cc4cccnc4Nc4ccccc43)c(Br)c2)n1 | null | O=C(c1ccc(F)cc1Br)N1Cc2cccnc2Nc2ccccc21 | Cc1cc[nH]n1 | null | [H-].[Na+].[CH3:3][C:4]1[CH:8]=[CH:7][NH:6][N:5]=1.[Br:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[C:17]([N:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][C:22]2[N:30]=[CH:31][CH:32]=[CH:33][C:21]=2[CH2:20]1)=[O:18]>CCCCCC>[Br:9][C:10]1[CH:15]=[C:14]([N:6]2[CH:7]=[CH:8][C:4]([CH3:3])=[N:5]2)[CH:13]=[CH:12][C:11]=1[C:17]([N:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[NH:23][C:22]2[N:30]=[CH:31][CH:32]=[CH:33][C:21]=2[CH2:20]1)=[O:18] | 0.67 | CCCCCC | null | null | null | null | 46.5 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,599,506 | Cl[Pd]Cl | null | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 7-(benzyloxy)-4-bromo-2,3-dihydro-1H-inden-1-one (520 mg, 1.64 mmol, 1.00 equiv), ethyl prop-2-enoate (825 mg, 8.24 mmol, 5.03 equiv), PdCl2 (58 mg, 0.33 mmol, 0.200 equiv), DIEA (1.06 g, 8.20 mmol, 5.00 equiv), (o-Tol)3P (201 mg, 0.66 mmol, 0.400 equiv), N,N-dimethylformamide (15 mL). The resulting solution was stirred for overnight at 90° C. in an oil bath. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The resulting solution was diluted with 20 mL of H2O. The resulting solution was extracted with 3×15 mL of ethyl acetate and the organic extracts were combined. The resulting mixture was washed with 1×15 mL of water and 1×15 mL of aqueous saturated sodium chloride solution. The mixture was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied to a silica gel column, eluting with ethyl acetate/petroleum ether (1:4). This resulted in 500 mg (86%) of ethyl (2E)-3-[7-(benzyloxy)-1-oxo-2,3-dihydro-1H-inden-4-yl]prop-2-enoate as a red solid. | CCOC(=O)/C=C/c1ccc(OCc2ccccc2)c2c1CCC2=O | null | O=C1CCc2c(Br)ccc(OCc3ccccc3)c21 | C=CC(=O)OCC | null | [CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22].CCN(C(C)C)C(C)C.CN(C)C=O>O.Cl[Pd]Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:22]=[CH:21]/[C:20]([O:24][CH2:25][CH3:26])=[O:23])=[C:13]2[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | 8 | O | CCN(C(C)C)C(C)C | CN(C)C=O | 90 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
420,109 | null | null | null | null | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | 1998-01-01T00:12:00 | true | 3-[4-[N,N-Bis(2-chloroethyl)amino]phenyl]propionic acid (0.24 g; 0.83 mmol) was dissolved in 5 ml of 1,2-dichloroethane, followed by the dropwise addition of 0.22 ml (2.58 mmol; 3.1 equivalents) of oxalyl chloride (with ice-cooling from an intermediary time point due to violent exotherm). After completion of the dropwise addition, the temperature of the resultant mixture was allowed to rise again to room temperature, at which the mixture was stirred for 3 hours and then allowed to stand overnight. The mixture was thereafter concentrated under reduced pressure, whereby the title compound was obtained in a crude form. The crude compound was provided for use in the next reaction without purification. | O=C(Cl)CCc1ccc(N(CCCl)CCCl)cc1 | null | O=C(Cl)C(=O)Cl | O=C(O)CCc1ccc(N(CCCl)CCCl)cc1 | null | [Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7].C(Cl)(=O)C([Cl:22])=O>ClCCCl>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([Cl:22])=[O:18])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7] | 3 | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
378,584 | [Li]CCCC | null | null | null | ord_dataset-846d411edee44814931e062174d7ef12 | 1997-01-01T00:09:00 | true | To a stirred solution of 4-(2-propyl)-oxazolidine-2-one in anhydrous tetrahydrofuran (250 ml) under a nitrogen atmosphere at -78° C. was added in a dropwise fashion a solution of n-butyllithium in hexane (50 ml, 77.4 mmol) over 5 to 10 min. After stirring an additional 20 min at -78° C., 4-methylpentanoyl chloride (85.2 mmol) was added neat. The reaction was warmed to room temperature and stirred 1 to 2 h at the temperature. The reaction was quenched by adding 100 ml of saturated aqueous ammonium chloride and the volatiles were removed by rotary evaporation. The resulting aqueous residue was extracted three times with ether and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from hexanes/ethyl acetate provided the desired compound. | CC(C)CCC(=O)N1C(=O)OC[C@@H]1C(C)C | null | CC(C)C1COC(=O)N1 | CC(C)CCC(=O)Cl | null | [CH3:1][CH:2]([CH:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.CCCCCC.[CH3:21][CH:22]([CH3:28])[CH2:23][CH2:24][C:25](Cl)=[O:26]>O1CCCC1>[CH3:21][CH:22]([CH3:28])[CH2:23][CH2:24][C:25]([N:5]1[C@@H:4]([CH:2]([CH3:3])[CH3:1])[CH2:8][O:7][C:6]1=[O:9])=[O:26] | 0.33 | C1CCOC1 | CCCCCC | null | -78 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,199,753 | null | null | null | null | ord_dataset-fb72428f30234761b4216139dc228d0c | 2012-01-01T00:09:00 | true | The title compound was prepared following procedure described for intermediate B1, but starting from 5-(3-furyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A2), 660 mg; 0.30 mmol; 1.0 eq.) and methoxyacetyl chloride (65 mg, 0.60 mmol; 2.0 eq.) as a white powder (59 mg, 72%). HPLC, Rt: 2.21 min. (purity 98.2%). LC/MS, M+(ESI): 273.4, M−(ESI): 271.4. | COCC(=O)Nc1nc2cccc(-c3ccoc3)n2n1 | null | COCC(=O)Cl | Nc1nc2cccc(-c3ccoc3)n2n1 | null | [O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]3[N:12]=[C:13]([NH2:15])[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[CH:2]1.[CH3:16][O:17][CH2:18][C:19](Cl)=[O:20]>>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:11]3[N:12]=[C:13]([NH:15][C:19](=[O:20])[CH2:18][O:17][CH3:16])[N:14]=[C:10]3[CH:9]=[CH:8][CH:7]=2)=[CH:2]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
229,627 | null | null | null | null | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | 1991-01-01T00:06:00 | true | A mixture of 1.44 g of 8-(p-chlorophenylsulfonamido-4-[3-(3-pyridyl)-propyl]-octanamide and 0.52 mL pyridine in 5.8 mL dioxane is cooled to 0° C. and 0.51 mL trifluoroacetic anhydride is added over a period of 1 hour. The mixture is then stirred at room temperature for 3 hours. The reaction is quenched by the addition of saturated aqueous sodium bicarbonate solution and extracted with methylene chloride (2×20 mL). The combined organic extracts are dried, filtered and evaporated to give 8-(p-chlorophenyl- sulfonamido)-4-[3-(3-pyridyl)propyl]octanenitrile. | N#CCCC(CCCCNS(=O)(=O)c1ccc(Cl)cc1)CCCc1cccnc1 | null | CCCCC(CCCc1cccnc1)CC(NS(=O)(=O)c1ccc(Cl)cc1)C(N)=O | c1ccncc1 | O=C(OC(=O)C(F)(F)F)C(F)(F)F | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH:17]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)CCCC)C(N)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:31]1C=C[CH:34]=[CH:33][CH:32]=1.F[C:38](F)(F)[C:39](OC(=O)C(F)(F)F)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:16][CH2:17][CH2:22][CH:23]([CH2:24][CH2:25][CH2:30][C:29]2[CH:28]=[N:27][CH:26]=[CH:38][CH:39]=2)[CH2:34][CH2:33][C:32]#[N:31])(=[O:9])=[O:10])=[CH:6][CH:7]=1 | 3 | C1COCCO1 | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,043,228 | CC(C)Oc1ccccc1O | O=C([O-])[O-] | [K+] | null | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | 2011-01-01T00:03:00 | true | 2-[3-(2-Isopropoxy-phenoxy)-propyl]-isoindole-1,3-dione. To a solution of 2-isopropoxy-phenol (0.50 g, 3.3 mmol) in DMF (5 mL) was added K2CO3 (2.3 g, 17 mmol), and the resulting suspension was stirred at 25° C. for 15 min. A solution of 2-(3-bromo-propyl)-isoindole-1,3-dione (0.97 g, 3.6 mmol) in DMF (2 mL) was added, and the reaction mixture was heated to 80° C. for 18 h. The mixture was filtered, and the filtrate was diluted with 1:1 Et2O/EtOAc (100 mL), washed with H2O (2×20 mL) then brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (5-20% EtOAc/hexanes) to provide the desired product (0.956 g, 87%). 1H NMR (400 MHz, CDCl3): 7.87-7.82 (m, 2H), 7.73-7.69 (m, 2H), 6.93-6.86 (m, 4H), 4.46 (hept, J=6.1 Hz, 1H), 4.06 (t, J=6.2 Hz, 2H), 3.92 (t, J=7.1 Hz, 2H), 2.20 (quint, J=6.4 Hz, 2H), 1.33 (d, J=6.1 Hz, 6H). | CC(C)Oc1ccccc1OCCCNCc1cccc(C(=O)N2CCCCC2)c1 | null | CC(C)Oc1ccccc1OCCCN1C(=O)c2ccccc2C1=O | O=C1c2ccccc2C(=O)N1CCCBr | null | [CH:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19](=O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)C1=O)([CH3:3])[CH3:2].C(OC1C=CC=CC=1O)(C)C.C([O-])([O-])=O.[K+].[K+].BrCCC[N:47]1[C:55](=[O:56])C2[C:49](=[CH:50][CH:51]=[CH:52]C=2)[C:48]1=O>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=1[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:19][C:18]1[CH:17]=[C:16]([C:55]([N:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)=[O:56])[CH:15]=[CH:14][CH:13]=1)([CH3:2])[CH3:3] | 0.25 | CN(C)C=O | null | null | 25 | 87 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
919,209 | O=[Pt]=O | null | null | null | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | 2009-01-01T00:11:00 | true | The title compound was prepared from {4-[4-(2-azido-propyl)-phenyl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine by hydrogenation using PtO2 in MeOH. Yield: 38 mg (81%). | CC(N)Cc1ccc(-c2ccnc(NC3CC(C)(C)NC(C)(C)C3)n2)cc1 | null | CC(Cc1ccc(-c2ccnc(NC3CC(C)(C)NC(C)(C)C3)n2)cc1)N=[N+]=[N-] | null | null | [N:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]3)[N:13]=2)=[CH:8][CH:7]=1)=[N+]=[N-]>CO.O=[Pt]=O>[NH2:1][CH:4]([CH3:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]3[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]3)[N:13]=2)=[CH:8][CH:7]=1 | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,457,248 | [Na+] | null | null | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | Crude (R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate was dissolved in MeOH/THF (50%, 5 mL). Aqueous NaOH (1N, 2 mL) was added. The reaction mixture was stirred at 50° C. for 16 h and was purified via preparative mass trigger LC-MS (AcCN/H2O, 20-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (34 mg, 38.9% from Step A starting material). 1H NMR (400 MHz, CD3OD) δ 1.22-1.32 (m, 9 H) 4.92 (br. s., 1 H) 5.18 (d, J=18.95 Hz, 1 H) 5.33 (d, J=18.95 Hz, 1 H) 7.88 (s, 1 H) 8.29 (s, 1 H). [M+H] calc'd for C15H16ClN3O3, 322; found, 322.5. | Cc1ccc(S(=O)(=O)n2cc(C(=O)O)c3c(CN[C@@H](C(=O)OCc4ccccc4)C(C)(C)C)c(Cl)cnc32)cc1 | null | [OH-] | Cc1ccc(S(=O)(=O)n2cc3c4c(c(Cl)cnc42)CN([C@@H](C(=O)OCc2ccccc2)C(C)(C)C)C3=O)cc1 | null | [Cl:1][C:2]1[C:11]2[CH2:10][N:9]([C@H:12]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[C:8](=[O:27])[C:7]3=[CH:28][N:29]([S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:5]([C:6]=23)=[N:4][CH:3]=1.[OH-:40].[Na+]>CO.C1COCC1>[CH2:16]([O:15][C:13](=[O:14])[C@H:12]([NH:9][CH2:10][C:11]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[N:29]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=3)(=[O:32])=[O:31])[CH:28]=[C:7]([C:8]([OH:40])=[O:27])[C:6]=12)[C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1 | 16 | C1CCOC1 | CO | null | 50 | null | 38.9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,457,936 | Cl | [Li+] | [O-2] | null | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | 2014-01-01T00:07:00 | true | To a solution of methyl 2-(2,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate (0.080 g; 0.246 mmol) in dioxane (4 mL) and water (1.5 mL) was added a 1N lithium oxide solution (1.5 mL; 1.50 mmol). The reaction mixture was heated at 60° C. for 4 h. After cooling to room temperature, the reaction mixture was acidified with 1N HCl (pH˜2) and partially concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was crystallized from a mixture of ethyl acetate/heptane to afford 0.037 g (48%) of the title compound as a beige solid. | Cc1ccc(-c2c(CC(=O)O)c(C)nc3sc(C)cc23)cc1 | null | COC(=O)Cc1c(C)nc2sc(C)cc2c1-c1ccc(C)cc1 | null | null | [CH3:1][C:2]1[S:23][C:5]2=[N:6][C:7]([CH3:22])=[C:8]([CH2:17][C:18]([O:20]C)=[O:19])[C:9]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)=[C:4]2[CH:3]=1.[O-2].[Li+].[Li+].Cl>O1CCOCC1.O>[CH3:1][C:2]1[S:23][C:5]2=[N:6][C:7]([CH3:22])=[C:8]([CH2:17][C:18]([OH:20])=[O:19])[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[C:4]2[CH:3]=1 | null | C1COCCO1 | O | null | 60 | null | 48.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
503,422 | Cl | null | null | null | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | 2001-01-01T00:05:00 | true | To a solution of 0.7716 g (1.8 mM) of N-methyl-N-(1-tert-butoxycarbonylpiperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide in ethanol (5 ml) was added 0.8 ml (9.6 mM) of 12N-hydrochloric acid at room temperature and the mixture was stirred for 18 hours. The solvent was then distilled off under reduced pressure, and 2 ml (24 mM) of 12N-hydrochloric acid was added to the residue. The mixture was stirred for 5 minutes, after which ethanol was added and the solvent was distilled off under reduced pressure. To the residue was further added ethanol and the ethanol, was distilled off under reduced pressure. The resulting crystals were collected by filtration and rinsed serially with ethanol, acetone, and diethyl ether to provide the title compound. | CN(CC1CCNCC1)C(=O)C1=Cc2cnc3cccc(n23)S1 | null | CN(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)C1=Cc2cnc3cccc(n23)S1 | null | null | [CH3:1][N:2]([CH2:17][CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1)[C:3]([C:5]1[S:15][C:14]2[N:16]3[C:7](=[CH:8][N:9]=[C:10]3[CH:11]=[CH:12][CH:13]=2)[CH:6]=1)=[O:4].[ClH:31]>C(O)C>[ClH:31].[ClH:31].[CH3:1][N:2]([CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:3]([C:5]1[S:15][C:14]2[N:16]3[C:7](=[CH:8][N:9]=[C:10]3[CH:11]=[CH:12][CH:13]=2)[CH:6]=1)=[O:4] | 18 | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
613,944 | Cl | null | null | null | ord_dataset-5c4ee54447b84205a10f9c0473172972 | 2003-01-01T00:10:00 | true | {3-[5-Methyl-3-(2-morpholinylsulfonylphenylsulfonyloxy)phenoxy]propoxy}guanidine hydrochloride: The title compound was prepared in 95% yield from 3-[5-methyl-[3-(2-morpholinylsulfonyl)phenylsulfonyloxy]phenoxy]propoxyamine, as prepared in the preceding step, in a manner analogous to step f of Example 1. 1H-NMR (300 MHz, DMSO-d6) δ 8.21 (t, J=8.0 Hz, 2H), 8.04 (t, J=7.8 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.71 (br s, 4H), 6.75 (s, 1H), 6.53 (s, 1H), 6.49 (s, 1H), 3.99 (t, J=6.3 Hz, 2H), 3.90 (t, J=6.4 Hz, 2H), 3.62 (t, J=4.7 Hz, 4H), 3.25 (t, J=4.7 Hz, 4H), 2.22 (s, 3H), 2.02 (t, J=6.3 Hz, 2H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C21H28N4O8S2: 529.1 (M+H), 551.1 (M+Na). Found: 528.9, 550.8. | CCOC(=O)C1CCN(S(=O)(=O)c2ccccc2S(=O)(=O)Oc2cc(C)cc(OCCCONC(=N)N)c2)CC1 | null | Cc1cc(OCCCONC(=N)N)cc(OS(=O)(=O)c2ccccc2S(=O)(=O)N2CCOCC2)c1 | N#CC(=Cc1ccc(O)cc1)C(=O)O | Cc1ccc(OS(=O)(=O)c2cccc(S(=O)(=O)C3CNCCO3)c2)c(OCCCON)c1 | [ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([N:31]2[CH2:36]COCC2)(=[O:30])=[O:29])(=[O:21])=[O:20])[CH:6]=[C:7]([CH:17]=1)[O:8][CH2:9][CH2:10][CH2:11][O:12][NH:13][C:14]([NH2:16])=[NH:15].[CH3:37][C:38]1C=CC(OS(C2C=CC=C(S(C3OCCNC3)(=O)=O)C=2)(=O)=O)=C(C=1)OCCCON.[C:69]([C:71](=[CH:75][C:76]1C=CC(O)=CC=1)[C:72]([OH:74])=[O:73])#N>>[ClH:1].[CH3:2][C:3]1[CH:4]=[C:5]([O:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[S:28]([N:31]2[CH2:76][CH2:75][CH:71]([C:72]([O:74][CH2:37][CH3:38])=[O:73])[CH2:69][CH2:36]2)(=[O:30])=[O:29])(=[O:21])=[O:20])[CH:6]=[C:7]([CH:17]=1)[O:8][CH2:9][CH2:10][CH2:11][O:12][NH:13][C:14]([NH2:16])=[NH:15] | null | null | null | null | null | 95 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,548,126 | CS(=O)(=O)Cl | [Na+] | null | null | ord_dataset-cac8df8aff894288876df4e093c9877f | 2015-01-01T00:02:00 | true | Under N2 atmosphere, 1-(4-(4-fluorophenoxy)pyrimidin-2-yl)ethanol (140 mg, 0.598 mmol) was dissolved in 3 mL anhydrous DCM. Triethylamine (0.175 mL, 1.26 mmol) was added, and the mixture was cooled to 0° C. MsCl (0.070 mL, 0.897 mmol) was added, and the mixture was stirred 15 minutes. Maintaining 0° C., DCM solvent was removed under N2 stream. Residue was taken up in 2 mL dry DMF. NaN3 (78 mg, 1.19 mmol) added, and the reaction was stirred at rt for 24 h. Mixture was poured into 20 mL water, and extracted with 20 mL EtOAc. Organic layer was washed with 20 mL brine and dried over Na2SO4. Filtered and concentrated to give 120 mg (77%) 2-(1-azidoethyl)-4-(4-fluorophenoxy)pyrimidine as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=5.7 Hz, 1H), 7.16-6.90 (m, 4H), 6.70 (d, J=5.7 Hz, 1H), 4.34 (q, J=6.9 Hz, 1H), 1.55-1.46 (m, 3H). | CC(N=[N+]=[N-])c1nccc(Oc2ccc(F)cc2)n1 | null | CC(O)c1nccc(Oc2ccc(F)cc2)n1 | [N-]=[N+]=[N-] | null | [F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH:13](O)[CH3:14])[N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>C(Cl)Cl.O>[N:30]([CH:13]([C:9]1[N:8]=[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)[CH:12]=[CH:11][N:10]=1)[CH3:14])=[N+:31]=[N-:32] | 0.25 | ClCCl | CCN(CC)CC | O | 0 | null | 77.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
605,602 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | c1c[nH]cn1 | null | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | 2003-01-01T00:08:00 | true | To a solution of 4-[1-(trimethylsilyloxy)ethyl]-2-pyridinecarbonitrile (39.04 g, 0.1624 mol) in THF (200 ml) was added a solution of tetrabutylammonium fluoride in THF (1M, 178.6 ml, 0.1786 mol) at room temperature. After stirring for 0.5 h, the mixture was concentrated. The residue was diluted with ethyl acetate (300 ml) and washed with water (200 ml). The aqueous layer was then extracted with dichloromethane (200 ml×2). The combined organic layers were dried (MgSO4) and concentrated. The residual oil was dissolved in DMF (200 ml). To the solution was added tert-butyldimethylsilylchloride (36.72 g, 0.2436 mol) and imidazole (22.11 g, 0.3248 mol) at room temperture. After stirring for 19 h, diethyl ether (500 ml) and water (200 ml) were added to the mixture and the organic layer was separated. The organic layer was washed with water (100 ml×2), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:20) to give 39.23 g (92%) of the title compound as an oil. | CC(O[Si](C)(C)C(C)(C)C)c1ccnc(C#N)c1 | null | CC(O[Si](C)(C)C)c1ccnc(C#N)c1 | CC(C)(C)[Si](C)(C)Cl | null | C[Si](C)(C)[O:3][CH:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]#[N:13])[CH:7]=1)[CH3:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].N1C=CN=C1>C1COCC1.O.C(OCC)C>[Si:34]([O:3][CH:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]#[N:13])[CH:7]=1)[CH3:5])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35] | 0.5 | O | C1CCOC1 | CCOCC | null | null | 92.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
377,146 | O=C([O-])[O-] | [Cs+] | null | null | ord_dataset-846d411edee44814931e062174d7ef12 | 1997-01-01T00:09:00 | true | 4-Phenylphenol (1.70 g, 10 mmol) and cesium carbonate (3.91 g (12 mmol) were stirred at room temperature under a nitrogen atmosphere in 20 mL of dimethylformamide until it appeared that no more solid was dissolving. At that point, 1.42 mL (12 mmol) of bromoacetaldehyde dimethyl acetal (2.03 g, 12 mmol) were added to the mixture via syringe and the resulting brown suspension was stirred at room temperature overnight. The mixture was then heated under reflux for two hours and then stirred at room temperature overnight. At the end of this period, 100 mL of water and 200 mL of diethyl ether were added; the organics were extracted into the ether layer, which was separated, dried over anhydrous sodium sulfate and evaporated to yield 2.10 g (81% yield) of dimethoxy-2-(4-biphenyloxy)ethane. | COC(C)(OC)Oc1ccc(-c2ccccc2)cc1 | null | Oc1ccc(-c2ccccc2)cc1 | COC(CBr)OC | null | [C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH2:23]Br.O>CN(C)C=O.C(OCC)C>[CH3:20][O:21][C:22]([O:25][CH3:26])([O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH3:23] | 8 | CCOCC | O | CN(C)C=O | 25 | null | 81.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
215,762 | null | null | null | null | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | 1990-01-01T00:09:00 | true | 6.9 g of 4-(2,3-dihydro-2,2-dimethyl-6-benzofuranylmethyloxy)aniline was dissolved into 70 ml of N,N-dimethylformamide, and 2.8 g of triethylamine was added thereto. 3.8 g of N-methoxy-N-methylcarbamoyl chloride was slowly added dropwise thereto. After the mixture was stirred at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water, it was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off and the residue was subjected to silica gel column chromatography using ethyl acetate/n-hexane (1/2) as a developer to obtain 6.0 g of Compound No. 4 shown in Table 1. | CON(C)C(=O)Nc1ccc(OCc2ccc3c(c2)OC(C)(C)C3)cc1 | null | CON(C)C(=O)Cl | CC1(C)Cc2ccc(COc3ccc(N)cc3)cc2O1 | null | [CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)=[CH:10][C:4]=2[O:3]1.CN(C)C=O.C(N(CC)CC)C.[CH3:33][O:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>O>[CH3:1][C:2]1([CH3:20])[CH2:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][O:12][C:13]3[CH:19]=[CH:18][C:16]([NH:17][C:36]([N:35]([O:34][CH3:33])[CH3:39])=[O:37])=[CH:15][CH:14]=3)=[CH:10][C:4]=2[O:3]1 | null | CN(C)C=O | CCN(CC)CC | O | 25 | 65.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
667,490 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | null | null | ord_dataset-c5ee194443334d3e92aff17e46e33bd1 | 2005-01-01T00:04:00 | true | To a stirred solution of (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl-(1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)benzyl]-2-hydroxypropylcarbamate (160 mg, 0.21 mmol) in tetrahydrofuran (3 mL) at 5° C. was added a mixture of tetrabutylammonium fluoride (0.3 mL, 1M in tetrahydrofuran) and glacial acetic acid (0.3 mL) over 2 minutes. The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The mixture was diluted with ethyl acetate (50 mL), washed with water (25 mL) followed by saturated sodium bicarbonate (20 mL) and then brine (20 mL), dried (magnesium sulfate) and concentrated in vacuo to afford the title compound (135 mg, quant.) as a white solid. 1H NMR (DMSO-d6): δ 0.78 (6H, dd), 1.17-1.42 (2H, m), 1.92 (1H, m), 2.33 (1H, t), 2.64-2.78 (3H, m), 2.89-3.02 (2H, m), 3.24-3.29 (1H, m), 3.52-3.73 (7H, m), 3.78-3.82 (1H, m), 3.86 (2H, t), 4.78-4.82 (2H, m), 4.99 (1H, d), 5.46 (1H, d), 6.12 (2H, s), 6.73 (2H, d), 7.02-7.28 (6H, m); MS: 637 (MH+) | CC(C)CN(C[C@@H](O)[C@H](Cc1ccc(OCCO)cc1)NC(=O)O[C@H]1CO[C@H]2OCC[C@H]21)S(=O)(=O)c1ccc2c(c1)OCO2 | null | CC(C)CN(C[C@@H](O)[C@H](Cc1ccc(OCCO[Si](C)(C)C(C)(C)C)cc1)NC(=O)O[C@H]1CO[C@H]2OCC[C@H]21)S(=O)(=O)c1ccc2c(c1)OCO2 | null | null | [O:1]1[C@H:5]2[O:6][CH2:7][CH2:8][C@H:4]2[C@@H:3]([O:9][C:10](=[O:51])[NH:11][C@@H:12]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][O:43][Si](C(C)(C)C)(C)C)=[CH:36][CH:35]=2)[C@H:13]([OH:32])[CH2:14][N:15]([S:20]([C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH2:28][O:29][C:25]=3[CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([S:20]([N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][C@@H:13]([OH:32])[C@@H:12]([NH:11][C:10](=[O:51])[O:9][C@@H:3]3[C@H:4]4[C@H:5]([O:6][CH2:7][CH2:8]4)[O:1][CH2:2]3)[CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][OH:43])=[CH:36][CH:35]=3)(=[O:22])=[O:21])=[CH:24][C:25]=2[O:29][CH2:28]1 | 18 | CCOC(C)=O | C1CCOC1 | CC(=O)O | 25 | 101 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
875,529 | Cl | O=C([O-])[O-] | [K+] | null | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | 2009-01-01T00:04:00 | true | In a tube is combined (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine [200 mg, 0.6 mmol, Intermediate (44)], nipecotic acid (194 mg, 1.5 mmol), K2CO3 (249 mg, 1.8 mmol) and 1-methyl-2-pyrrolidinone (2.5 mL). The tube is sealed and heated to 140° C. and stirred for 5 hours. The mixture is allowed to cool to ambient temperature, stand for 12 hours, diluted with water (20 mL) and acidified using 3M HCl. A precipitate forms and is collected by filtration and dried under high vacuum to afford 1-{6-[2-(2,4-dichloro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-piperidine-3-carboxylic acid [121 mg, 47%, Example 73] as a solid. LCMS RT=2.15 minutes, MS: 425 (M+H). IC50=0.8 nM | COc1nc(NCCc2ccc(Cl)cc2Cl)cc(N2CCCC(C(=O)O)C2)n1 | null | O=C(O)C1CCCNC1 | COc1nc(Cl)cc(NCCc2ccc(Cl)cc2Cl)n1 | null | Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:3]=1.[NH:21]1[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([OH:26])=[O:25])[CH2:22]1.C([O-])([O-])=O.[K+].[K+].Cl>O.CN1CCCC1=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][NH:10][C:4]1[N:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([N:21]2[CH2:29][CH2:28][CH2:27][CH:23]([C:24]([OH:26])=[O:25])[CH2:22]2)[CH:3]=1 | 5 | CN1CCCC1=O | O | null | 140 | null | 47.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,683,719 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | A flask is charged with N-[5-(6-chloro-1H-indol-2-yl)-pyridin-3-ylmethyl]-methanesulfonamide (670 mg, 1.49 mmol), DMF (10 mL), dimethyl carbonate (403 mg, 4.47 mmol) and potassium carbonate (319 mg, 2.31 mmol), and the mixture is stirred at 150° C. for 5 h. The mixture is cooled to room temperature and purified using Xbridge C18 eluting with a 1:9 to 9:1 acetonitrile-water gradient to give N-[5-(6-chloro-1H-indol-2-yl)-pyridin-3-ylmethyl]-N-methyl-methanesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.74 (s, 3H), 3.02 (s, 3H), 4.35 (s, 2H), 7.04 (dd, J=8.5, 1.9 Hz, 1H), 7.09 (d, J=1.5 Hz, 1H), 7.43 (d, J=1.8 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 8.14 (t, J=2.1 Hz, 1H), 8.47 (d, J=2.0 Hz, 1H), 9.05 (d, J=2.3 Hz, 1H), 11.92 (s, 1H). HRMS (ESI) m/z 350.0738 [(M+H)+ Calcd for C16H17ClN3O2S: 350.0730]. | CN(Cc1cncc(-c2cc3ccc(Cl)cc3[nH]2)c1)S(C)(=O)=O | null | CS(=O)(=O)NCc1cncc(-c2cc3ccc(Cl)cc3[nH]2)c1 | COC(=O)OC | null | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:12]=[C:13]([CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=[N:15][CH:16]=3)[NH:8]2)=[CH:4][CH:3]=1.[C:23](=O)(OC)OC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:12]=[C:13]([CH2:17][N:18]([CH3:23])[S:19]([CH3:22])(=[O:20])=[O:21])[CH:14]=[N:15][CH:16]=3)[NH:8]2)=[CH:4][CH:3]=1 | 5 | CN(C)C=O | null | null | 150 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,186,866 | [Pd] | null | null | null | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | 2012-01-01T00:07:00 | true | A suspension of 5-nitro-m-xylene (1.51 g) and 10% Pd/C (80 mg) in MeOH (50 mL) was stirred at room temperature under H2 balloon for 16 h. The reaction mixture was filtered through a Celite pad, washed with EtOAc, concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=5:95 to 40:60) to give 3,5-dimethyl-phenylamine as a yellow oil: MS (m/z) 122 (M+1); 1H NMR (CDCl3, 400 MHz) δ 6.41 (s, 1H), 6.33 (s, 2H), 3.52 (s, 2H), 2.22 (s, 6H). | Cc1cc(C)cc(N)c1 | null | Cc1cc(C)cc([N+](=O)[O-])c1 | null | null | [N+:1]([C:4]1[CH:5]=[C:6]([CH3:11])[CH:7]=[C:8]([CH3:10])[CH:9]=1)([O-])=O>CO.[Pd]>[CH3:10][C:8]1[CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]([CH3:11])[CH:7]=1 | 16 | CO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,629,552 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | 2015-01-01T00:09:00 | true | A mixture of 4-chloro-1-[4-hydroxy-2-((S)-3-hydroxymethyl-3,4-dihydro-1H-isoquinoline-2-carbonyl)-phenyl]-5-methyl-1H-pyrazole-3-carboxylic acid dibutylamide (intermediate D, 170 mg, 0.31 mmol), ethyl 2-iodoacetate (99 mg, 0.46 mmol), potassium carbonate (13 mg, 0.092 mmol), and triethylamime (0.085 mL, 0.62 mmol) was stirred in acetonitrile (3 mL) at ambient temperature for 12 hours. The solvent was removed in vacuo. The crude material was purified by eluting through a silica gel column with a 10 to 100% ethyl acetate/heptane gradient to afford the title compound (15 mg, 7.6% yield). MS (ESI) [m/e, (M+H)+]=639.3. 1H NMR (400 MHz, chloroform-d) δ ppm 6.73-7.39 (m, 7H), 2.51-5.41 (m, 17H), 2.16-2.41 (m, 3H), 0.68-1.70 (m, 16H). | CCCCN(CCCC)C(=O)c1nn(-c2ccc(OCC(=O)OCC)cc2C(=O)N2Cc3ccccc3C[C@H]2CO)c(C)c1Cl | null | CCCCN(CCCC)C(=O)c1nn(-c2ccc(O)cc2C(=O)N2Cc3ccccc3C[C@H]2CO)c(C)c1Cl | CCOC(=O)CI | null | [CH2:1]([N:5]([CH2:36][CH2:37][CH2:38][CH3:39])[C:6]([C:8]1[C:12]([Cl:13])=[C:11]([CH3:14])[N:10]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[C:22]([N:24]2[C@H:33]([CH2:34][OH:35])[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].I[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:45]([O:44][C:42](=[O:43])[CH2:41][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:10]2[C:11]([CH3:14])=[C:12]([Cl:13])[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:36][CH2:37][CH2:38][CH3:39])=[N:9]2)=[C:16]([C:22]([N:24]2[C@H:33]([CH2:34][OH:35])[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25]2)=[O:23])[CH:17]=1)[CH3:46] | null | CC#N | null | null | null | null | 7.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
522,000 | COc1ccc([C@@H](Sc2ccccc2[N+](=O)[O-])[C@H](O)C(=O)O)cc1 | null | null | null | ord_dataset-262b40ea420c471da9b9244fe9b8f645 | 2001-01-01T00:10:00 | true | By treating (±)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine and (2R,3R)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitrophenylthio)propionic acid in the same manner as in Example 4-(1), (2) and (3) to afford (S)-4-[(4-chlorophenyl) (2-pyridyl)methoxy]piperidine. | Clc1ccc([C@H](OC2CCNCC2)c2ccccn2)cc1 | null | Clc1ccc(C(OC2CCNCC2)c2ccccn2)cc1 | null | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.O[C@@H]([C@@H](C1C=CC(OC)=CC=1)SC1C=CC=CC=1[N+]([O-])=O)C(O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[CH:4][CH:3]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,593,105 | null | null | null | null | ord_dataset-e8c6a25568b64529b960953990e6921f | 2015-01-01T00:06:00 | true | 3-((5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one P11 was synthesized following the procedure reported for the synthesis of 3-((3-bromo-1-(3-(methylsulfonyl)propyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one P17, using (5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol 10 instead of (3-bromo-1-(3-(methylsulfonyl)propyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)methanol 12. 1H NMR (360 MHz, DMSO-d6) δ ppm 0.87-0.97 (m, 2H), 1.02-1.13 (m, 2H), 1.57-1.78 (m, 4H), 2.99 (tt, J=6.9, 3.6 Hz, 1H), 4.30-4.43 (m, 3H), 4.49 (m, J=5.7, 5.7 Hz, 1H), 5.35 (s, 2H), 6.53 (s, 1H), 7.29 (d, J=5.5 Hz, 1H), 7.56 (s, 1H), 8.26 (d, J=5.1 Hz, 1H), 8.37 (s, 1H), 8.70 (s, 1H); m/z=414 (M+H)+. | O=c1n(Cc2cc3cc(Cl)ncc3n2CCCCF)c2cnccc2n1C1CC1 | null | CS(=O)(=O)CCCn1c(Cn2c(=O)n(C3CC3)c3ccncc32)c(Br)c2cnccc21 | OCc1cc2cc(Cl)ncc2n1CCCCF | null | BrC1C2C=NC=CC=2N(CCCS(C)(=O)=O)C=1C[N:19]1[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:22]=2[N:21]([CH:28]2[CH2:30][CH2:29]2)[C:20]1=[O:31].[Cl:32][C:33]1[CH:34]=[C:35]2[CH:41]=[C:40]([CH2:42]O)[N:39]([CH2:44][CH2:45][CH2:46][CH2:47][F:48])[C:36]2=[CH:37][N:38]=1>>[Cl:32][C:33]1[CH:34]=[C:35]2[CH:41]=[C:40]([CH2:42][N:19]3[C:23]4[CH:24]=[N:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]4[CH2:29][CH2:30]4)[C:20]3=[O:31])[N:39]([CH2:44][CH2:45][CH2:46][CH2:47][F:48])[C:36]2=[CH:37][N:38]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,391,160 | [F-] | [K+] | null | null | ord_dataset-31641fb65b34430fa7435229b949b604 | 2014-01-01T00:01:00 | true | To a suspension of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 0.050 g, 0.12 mmol) and potassium fluoride (0.010 g, 0.18 mmol) in dry benzene (6 ml) was added 1-bromo-2-isocyanatobenzene (0.036 g, 0.12 mmol) at RT. The reaction was stirred at reflux temperature for 6 hours. The reaction mixture was cooled and poured into cold water, extracted with ethyl acetate (2×20 ml). Organic layer was washed with water dried over sodium sulfate and concentrated. The crude product was crystallized in ethyl acetate\pet ether to obtain the title compound. Yield: 0.017 g (22%); 1H NMR (DMSO-d6, 300 MHz): δ 11.82 (s, 1H), 8.78 (s, 1H), 7.90 (d, 1H, J=9 Hz), 7.81 (d, 2H, J=8.1 Hz), 7.61-7.65 (m, 3H), 7.28 (d, 1H, J=8.1 Hz), 6.95-7.05 (m, 2H), 6.74 (d, 1H, 7.8 Hz), 6.41 (t, 1H, 7.2 Hz), 1.79 (s, 6H); MS: m/z 606 (M+). | CC(C)(C#N)c1ccc(-n2c(=O)n(C(=O)Nc3ccccc3Br)c3cnc4ccc(Br)cc4c32)cc1 | null | O=C=Nc1ccccc1Br | CC(C)(C#N)c1ccc(-n2c(=O)[nH]c3cnc4ccc(Br)cc4c32)cc1 | null | [Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.[F-].[K+].[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]=[C:37]=[O:38].O>C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([C:37]([NH:36][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[Br:29])=[O:38])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([C:22]#[N:23])([CH3:24])[CH3:25])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1 | null | c1ccccc1 | O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
462,247 | O=C([O-])[O-] | [K+] | null | null | ord_dataset-5ca9db262dd24c5a9315cdc8ef055b7e | 2000-01-01T00:04:00 | true | A mixture of 2-fluoro-4-hydroxybenzonitrile (S. M. Kelly, Helv.Chim.Acta. 1984, Volume 67, P.1572-1579) (30 g), potassium carbonate (45.36 g) and 3,4-methylenedioxybenzyl chloride (42.65 g) in dimethylformamide (500 ml) was stirred at 90° C. for 2 hours. The reaction mixture was filtered and the filtrate evaporated. The residue was stirred with ethyl acetate (500 ml) and filtered affording the title compound (32.1 g) as a cream coloured solid, m.p. 139-140° C. | N#Cc1ccc(OCc2ccc3c(c2)OCO3)cc1F | null | N#Cc1ccc(O)cc1F | ClCc1ccc2c(c1)OCO2 | null | [F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17]1[O:27][C:26]2[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][C:19]=2[O:18]1>CN(C)C=O>[O:27]1[C:26]2[CH:25]=[CH:24][C:21]([CH2:22][O:10][C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=3)=[CH:20][C:19]=2[O:18][CH2:17]1 | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
147,965 | NCCNc1cccc2[nH]ncc12 | c1ccc(COc2ccc(OCC3CO3)cc2)cc1 | null | null | ord_dataset-2069a3db775a4d9f9310aca092ecbad8 | 1986-01-01T00:08:00 | true | The 1-(4-benzyloxyphenoxy)-3-[2-(indazol-4-ylamino)-ethylamino]-propan-2-ol used as starting material can be obtained in the following manner: 5.1 g. 4-benzyloxyphenyl glycidyl ether and 7.0 g. 4-(2-aminoethylamino)-indazole are dissolved in 10 ml. dimethylformamide and left to stand for 2 days at ambient temperature. The reaction mixture is then digested by the addition of 20 ml. methanol, filtered off with suction and then washed with methanol. There are obtained 5.0 g. (58% of theory) of the desired product in the form of colorless crystals; m.p. 151°-153° C. | Oc1ccc(OCC(O)CNCCNc2cccc3[nH]ncc23)cc1 | null | OC(CNCCNc1cccc2[nH]ncc12)COc1ccc(OCc2ccccc2)cc1 | null | null | C([O:8][C:9]1[CH:32]=[CH:31][C:12]([O:13][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(OC1C=CC(OCC2C=CC=CC=2)=CC=1)C1OC1.NCCNC1C=CC=C2C=1C=NN2>CN(C)C=O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH:15]([OH:30])[CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[N:24][NH:25]3)=[CH:31][CH:32]=1 | 48 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,681,114 | CC[O-] | O=C([O-])O | [Na+] | null | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | 2016-01-01T00:01:00 | true | A solution of 6-bromoquinoline-5-carbonitrile (16b) (300 mg, 1.29 mmol), ethyl mercaptoacetate (212 μL, 1.93 mmol) and sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 15 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. It was extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The intermediate ethyl 2-[(5-cyanoquinolin-6-yl)sulfanyl]acetate obtained was reacted with sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (8 mL) by stirring at 90° C. for 3 hours. The reaction was cooled to room temperature and water was added (10 mL). The resulting precipitate was filtered and washed with water twice and dried under vacuum with phosphorus pentoxide to afford the desired product (16c) as a solid (299 mg, 1.10 mmol, 85%). | CCOC(=O)CSc1ccc2ncccc2c1C#N | null | CCOC(=O)CS | N#Cc1c(Br)ccc2ncccc12 | null | Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]#[N:13].[SH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:12]([C:3]1[C:2]([S:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)#[N:13] | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
228,937 | null | null | null | null | ord_dataset-9adbd9cd2fd941f7af27fb31c9bf3bac | 1991-01-01T00:06:00 | true | A solution of 0.5 g of (S,S)-2,4-dibenzylglutaric anhydride and 0.82 g of O-benzyl-(L)-serine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester in 10 ml of methylene chloride is stirred at room temperature overnight. The solution is diluted with ether, washed with 1N hydrochloric acid, water, dried (Na2S04), filtered and concentrated to give N-[(S,S)-2,4-dibenzyl-4-carboxybutyryl]-O-benzyl-(L)-serine 1,2:5,6-di-O-isopropylidene-D-glucofuranos-3-yl ester melting at 55°-58°; [α]D =+2.2°. | O=C(O)[C@H](Cc1ccccc1)C[C@@H](Cc1ccccc1)C(=O)N[C@@H](COCc1ccccc1)C(=O)O | null | N[C@@H](COCc1ccccc1)C(=O)O | O=C1OC(=O)[C@H](Cc2ccccc2)C[C@H]1Cc1ccccc1 | null | [CH2:1]([C@@H:8]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:22])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:30][CH2:31][C@@H:32]([C:34]([OH:36])=[O:35])[NH2:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl.CCOCC>[CH2:15]([C@H:13]([CH2:14][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([OH:11])=[O:10])[C:12]([NH:33][C@H:32]([C:34]([OH:36])=[O:35])[CH2:31][O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1 | null | CCOCC | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,741,605 | BrB(Br)Br | N | null | null | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | 2016-01-01T00:06:00 | true | 5-bromo-1-cyclopropyl-7-methoxy-1H-benzo[d]imidazole (0.54 g, 2.01 mmol) was dissolved in dichloromethane (12 mL) under N2. A 1M BBr3 solution in DCM (12 mL, 12 mmol) was added dropwise over 1 min. The resulting stirred suspension was heated to 35° C. After 5 h, the reaction mixture was cooled in an ice water bath. A 7M ammonia in MeOH solution (7.5 mL, 53 mmol) was then added over 2 min via syringe. The mixture was stirred 5 min and was removed from the ice bath. After an additional 10 min, the mixture was concentrated in vacuo, and the crude product was dissolved in MeOH (30 mL) and was concentrated in vacuo. The resulting crude solids were suspended in 20% MeOH in DCM (30 mL) and were filter through a short pad of silica, eluting with 20% MeOH in DCM. Filtrate was concentrated in vacuo, and the crude product was adsorbed onto silica gel. Purification by silica gel chromatography (0-20% MeOH in DCM) gave 5-bromo-1-cyclopropyl-1H-benzo[d]imidazol-7-ol (2.73). LCMS-ES r (m/z): [m+H]+ calcd for C10H10BrN2O: 253.00; found: 253.14. | Oc1cc(Br)cc2ncn(C3CC3)c12 | null | COc1cc(Br)cc2ncn(C3CC3)c12 | null | null | [Br:1][C:2]1[CH:13]=[C:12]([O:14]C)[C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.N.CO>ClCCl>[Br:1][C:2]1[CH:13]=[C:12]([OH:14])[C:5]2[N:6]([CH:9]3[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1 | 5 | CO | ClCCl | null | 35 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,342,345 | O=S(=O)(O)O | null | null | null | ord_dataset-08852243bba44cb28769a5833f1515fe | 2013-01-01T00:09:00 | true | 4-Hydroxy-3-iodobenzonitrile was prepared by the method analogous to Preparation 341 above using N-iodosuccinimide, acetic acid, sulfuric acid and 4-Hydroxybenzonitrile. Purified by ISCO™ (80 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 3:7, by volume) to yield the title compound. | N#Cc1ccc(O)c(I)c1 | null | O=C1CCC(=O)N1I | N#Cc1ccc(O)cc1 | null | [I:1]N1C(=O)CCC1=O.S(=O)(=O)(O)O.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1>C(O)(=O)C>[OH:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[I:1] | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,241,437 | CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC | On1nnc2ccccc21 | null | null | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | 2013-01-01T00:01:00 | true | 3-[(4-Methoxybenzyl)oxy]benzoic acid (9.26 g, 35.9 mmol), acethydrazide (3.98 g, 53.8 mmol), HOBT (6.59 g, 43 mmol) and EDC (10.3 g, 53.8 mmol) were weighed into a 200 mL RB flask. DMF (60 mL) was added. The mixture was stirred vigorously at room temperature. The solid dissolved within 5 min. LC-MS showed complete consumption of the acid after 30 min. DMF was removed at 60° C. under vacuum. The residue was treated with 100 mL EtOAc/water (1/1) and was allowed to stand overnight. The solid was collected via filtration and washed with EtOAc. The crude N′-acetyl-3-[(4-methoxybenzyl)oxy]benzohydrazide (8 g) was suspended in 100 mL THF and was heated under reflux in the presence of Burgess' reagent (12.8 g, 53.8 mmol) for 1 hour. The solution was cooled and directly passed through a plug of silica gel (300 gram) which was washed thoroughly with 20% acetone/hexanes. The eluent was concentrated to give the crude product as white solid. | COc1ccc(COc2cccc(-c3nnc(C)o3)c2)cc1 | null | CC(=O)NN | COc1ccc(COc2cccc(C(=O)O)c2)cc1 | null | [CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)=[CH:5][CH:4]=1.[C:20]([NH:23][NH2:24])(=O)[CH3:21].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:12]3[O:14][C:20]([CH3:21])=[N:23][N:24]=3)[CH:15]=[CH:16][CH:17]=2)=[CH:18][CH:19]=1 | 8 | ClCCCl | CN(C)C=O | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,292,207 | null | null | null | null | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | 2013-01-01T00:05:00 | true | This compound was prepared by using procedures analogous to those described for the synthesis of Example 30 starting from 4-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine and 1-acetylpiperazine (Aldrich Cat. No. 359513). LCMS (M+H)+: m/z=451.2. | CC(=O)N1CCN(c2ccc3c(c2)CN(c2cc(N4CCN(C)CC4)nc(N)n2)CC3)CC1 | null | CC(=O)N1CCNCC1 | CN1CCN(c2cc(N3CCc4ccc(Br)cc4C3)nc(N)n2)CC1 | null | Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.[C:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])[CH3:27]>>[C:26]([N:29]1[CH2:34][CH2:33][N:32]([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([C:12]4[CH:17]=[C:16]([N:18]5[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]5)[N:15]=[C:14]([NH2:25])[N:13]=4)[CH2:9]3)=[CH:4][CH:3]=2)[CH2:31][CH2:30]1)(=[O:28])[CH3:27] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
620,662 | Cl | null | null | null | ord_dataset-c9f990dde2dc45d0948ecbe037a0d819 | 2004-01-01T00:01:00 | true | In analogy to the procedure described in example 20b, 4-chloro-2,6-bis-(2-hydroxy-ethylamino)-pyrimidine-5-carbonitrile was treated with 4-phenyl-1,2,3,6-tetrahydro-pyridine hydrochloride in ethanol in the presence of N-ethyl-diisopropylamine at 80° C. to yield 2,4-bis-(2-hydroxy-ethylamino)-6-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-pyrimidine-5-carbonitrile as an amorphous, brown solid; MS: [M+H]+=381. | N#Cc1c(NCCO)nc(NCCO)nc1N1CC=C(c2ccccc2)CC1 | null | N#Cc1c(Cl)nc(NCCO)nc1NCCO | C1=C(c2ccccc2)CCNC1 | null | Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[N:5]=[C:4]([NH:14][CH2:15][CH2:16][OH:17])[N:3]=1.Cl.[C:19]1([C:25]2[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)C(C)C)C>C(O)C>[OH:17][CH2:16][CH2:15][NH:14][C:4]1[N:5]=[C:6]([NH:10][CH2:11][CH2:12][OH:13])[C:7]([C:8]#[N:9])=[C:2]([N:28]2[CH2:27][CH:26]=[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:30][CH2:29]2)[N:3]=1 | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
604,216 | [Na+] | [OH-] | null | null | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | 2003-01-01T00:08:00 | true | Using General Procedure I; a solution of ethyl 4-{4-[1-(benzylmethylamino)-cyclopropyl]-phenylethynyl}-benzoate (Compound 115, 65.0 mg, 0.16 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 45.0 mg (75%) of the title compound as a solid. | O=C(O)c1ccc(C#Cc2ccc(C3(NCCc4ccccc4)CC3)cc2)cc1 | null | CCOC(=O)c1ccc(C#Cc2ccc(C3(NCCc4ccccc4)CC3)cc2)cc1 | null | null | [CH2:1]([CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:1]([CH2:8][NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]3[CH:31]=[CH:30][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:11][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | 8 | C1CCOC1 | CCO | null | 25 | null | 73.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
377,789 | null | null | null | null | ord_dataset-846d411edee44814931e062174d7ef12 | 1997-01-01T00:09:00 | true | A 100 mL one-neck round-bottom flask equipped for magnetic stirring was charged with 2-bromo-2-(4-methylthiophenyl)-1(4-methylphenyl)ethanone from Step 3 (0.300 g, 0.895 mmol) and acetonitrile (20 mL). 2-Chlorothiobenzamide (0.154 g, 0.895 mmol) was added, and the suspension was heated and held at reflux for three hours. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and poured into water(50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic solution was dried over MgSO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (silica gel; 5% ethyl acetate in hexane) to yield 2-(2-chlorophenyl)-4-(4-methylphenyl)-5-(4-methylthiophenyl)thiazole (0.284 g, 78%) as a white solid: mp 125°-126° C. 1H NMR (CDCl3) 300 MHz 8.40(m, 1H), 7.62-7.11(m, 11H), 2.50 (s, 3H), 3.36(s, 3H). Mass spectrum: MH+ =407. | CSc1ccc(-c2sc(-c3ccccc3Cl)nc2-c2ccc(C)cc2)cc1 | null | NC(=S)c1ccccc1Cl | CSc1ccc(C(Br)C(=O)c2ccc(C)cc2)cc1 | null | Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.C(#N)C.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH2:28])=[S:27].O>C(OCC)(=O)C>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]1[S:27][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=2)[N:28]=1 | null | CCOC(C)=O | CC#N | O | 25 | null | 77.8 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,362,030 | [Na+] | [OH-] | null | null | ord_dataset-d932d1d683704a8bad3d064bcb197acc | 2013-01-01T00:11:00 | true | To a solution of 2-ethyl-4-[5-(2-ethyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol (89 mg, 0.276 mmol) in 3 N aq. NaOH (1 mL) and isopropanol (4 mL), (R)-epichlorohydrine (142 mg, 1.53 mmol) is added. The mixture is stirred at rt for 24 h before another portion of (R)-epichlorohydrine (142 mg; 1.53 mmol) is added. Stirring is continued for another 24 h at rt. The mixture is diluted with EA (50 mL) and washed with 1M aq. NaOH (10 mL) and brine (10 mL). The org. phase is dried over MgSO4, filtered and evaporated to give crude (S)-2-ethyl-4-[3-(3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine; LC-MS*: tR=1.11* min; [M+1]+=380.24. | CCc1cc(-c2nc(-c3cc(C)c(OC[C@@H]4CO4)c(CC)c3)no2)cc(C)n1 | null | CCc1cc(-c2nc(-c3cc(C)c(O)c(CC)c3)no2)cc(C)n1 | ClC[C@H]1CO1 | null | [CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([CH2:21][CH3:22])[CH:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:23])[C:4]=1[OH:24])[CH3:2].[CH2:25]([C@@H:27]1[O:29][CH2:28]1)Cl>[OH-].[Na+].C(O)(C)C.CC(=O)OCC>[CH2:21]([C:16]1[CH:15]=[C:14]([C:12]2[O:11][N:10]=[C:9]([C:7]3[CH:6]=[C:5]([CH3:23])[C:4]([O:24][CH2:25][C@@H:27]4[CH2:28][O:29]4)=[C:3]([CH2:1][CH3:2])[CH:8]=3)[N:13]=2)[CH:19]=[C:18]([CH3:20])[N:17]=1)[CH3:22] | 24 | CCOC(C)=O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
55,198 | null | null | null | null | ord_dataset-159c363342e44b539e7a5975c873e30d | 1979-01-01T00:05:00 | true | This titled benzamide was prepared according to the general acid chloride method described above on a 0.01 mol scale by reacting the trans-2-[N-(2-furylmethyl)methylamino]cyclohexylamine, prepared as described in part (a) above with 3,4-dichlorobenzoyl chloride. The reaction product mixture was extracted with methylene dichloride to extract the benzamide product therefrom. The crude product was chromatographed on 380 g. of silica gel using a 1 percent methanol-in-chloroform eluant. Fraction 1 (1000 m.) and fractions 2 to 17 (25 ml. each) gave no material. Fractions 18 to 54 (25 ml. each) gave a solid which was crystallized from ether giving colorless needles, 1.91 g., (50% yield) of the named benzamide product, melting point 149°-150° C. The Ultraviolet, Infrared, and Nuclear Magnetic Resonance spectral analyses were consistent for the named benzamide. | CN(Cc1ccco1)[C@@H]1CCCC[C@H]1NC(=O)c1ccc(Cl)c(Cl)c1 | null | CN(Cc1ccco1)[C@@H]1CCCC[C@H]1N | O=C(Cl)c1ccc(Cl)c(Cl)c1 | null | [O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([CH3:15])[C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20](Cl)=[O:21]>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[Cl:26])[C:20]([NH:14][C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][C@H:8]1[N:7]([CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH3:15])=[O:21] | null | null | null | null | null | 50 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
602,441 | Cc1ccc(S(=O)(=O)O)cc1 | O=C([O-])O | [Na+] | null | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | 2003-01-01T00:07:00 | true | 100 μl of hydrazine hydrate and 3 mg of paratoluenesulphonic acid are added to 300 mg of the product obtained in Example 73 in 3 cm3 of methanol. Agitation is carried out for 16 hours at ambient temperature, 50 cm3 of an aqueous solution of sodium bicarbonate is added, extraction is carried out with methylene chloride, the solvent is evaporated off, the residue is chromatographed on silica (eluant: ethyl acetate) and 190 mg of expected product is obtained. | C[C@]12C[C@H](c3ccc(OCCCCCS(=O)(=O)CCCC(F)(F)C(F)(F)F)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=NN | null | NN | C[C@]12C[C@H](c3ccc(OCCCCCS(=O)(=O)CCCC(F)(F)C(F)(F)F)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O | null | O.[NH2:2][NH2:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][C@@H:29]3[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][S:46]([CH2:49][CH2:50][CH2:51][C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])(=[O:48])=[O:47])=[CH:36][CH:35]=3)([CH3:27])[C:25](=O)[CH2:24][CH2:23]4)[CH2:20][CH2:19][C:18]=2[CH:17]=1.C(=O)(O)[O-].[Na+]>CO>[OH:15][C:16]1[CH:33]=[CH:32][C:31]2[C@@H:30]3[C@H:21]([C@H:22]4[C@@:26]([CH2:28][C@@H:29]3[C:34]3[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][S:46]([CH2:49][CH2:50][CH2:51][C:52]([F:58])([F:57])[C:53]([F:56])([F:55])[F:54])(=[O:48])=[O:47])=[CH:36][CH:35]=3)([CH3:27])[C:25](=[N:2][NH2:3])[CH2:24][CH2:23]4)[CH2:20][CH2:19][C:18]=2[CH:17]=1 | 16 | O | CO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,474,632 | null | null | null | null | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | 2014-01-01T00:09:00 | true | The mixture of 5-[3-Amino-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-1-methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one (0.2 g, 0.36 mmol), 4-bromo-2-(2-bromo-ethyl)-benzenesulfonyl chloride (0.4 g, 1.08 mmol) and DIPEA (1 mL) in dichloroethane (10 mL) was microwaved at 120° C. for 30 min, then added 4-bromo-2-(2-bromo-ethyl)-benzenesulfonyl chloride (0.4 g, 1.08 mmol) and DIPEA (1 mL) and microwaved at 120° C. for 30 min. After repeating this process three times, the mixture was concentrated to afford a dark residue. Purification by silica gel chromatography (methylene chloride/acetone) afforded 0.15 g of 5-[3-(6-Bromo-1,1-dioxo-3,4-dihydro-1H-1lambda*6*-benzo[e][1,2]thiazin-2-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-1H-pyridin-2-one as a pale solid MS (ESI) 796.2 (M+H)+. | CC(C)(C)[SiH2]OC(C)(C)c1c(-c2c[nH]c(=O)c(Nc3ccc(C(=O)N4CCOCC4)cn3)c2)cccc1N1CCc2cc(Br)ccc2S1(=O)=O | null | O=S(=O)(Cl)c1ccc(Br)cc1CCBr | Cn1cc(-c2cccc(N)c2C(C)(C)O[SiH2]C(C)(C)C)cc(Nc2ccc(C(=O)N3CCOCC3)cn2)c1=O | null | [NH2:1][C:2]1[C:3]([C:31]([CH3:39])([CH3:38])[O:32][SiH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[C:4]([C:8]2[CH:9]=[C:10]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:24])=[CH:19][N:18]=3)[C:11](=[O:15])[N:12](C)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[Br:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[C:43]([CH2:51][CH2:52]Br)[CH:42]=1.CCN(C(C)C)C(C)C>ClC(Cl)C>[Br:40][C:41]1[CH:46]=[CH:45][C:44]2[S:47](=[O:49])(=[O:48])[N:1]([C:2]3[C:3]([C:31]([CH3:39])([CH3:38])[O:32][SiH2:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[C:4]([C:8]4[CH:9]=[C:10]([NH:16][C:17]5[CH:22]=[CH:21][C:20]([C:23]([N:25]6[CH2:26][CH2:27][O:28][CH2:29][CH2:30]6)=[O:24])=[CH:19][N:18]=5)[C:11](=[O:15])[NH:12][CH:13]=4)[CH:5]=[CH:6][CH:7]=3)[CH2:52][CH2:51][C:43]=2[CH:42]=1 | null | CCN(C(C)C)C(C)C | CC(Cl)Cl | null | null | null | 53.4 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
309,877 | Cl | null | null | null | ord_dataset-081613ef79bd4110aacc146b4465f086 | 1995-01-01T00:05:00 | true | To 5 ml of a methylene chloride solution of 149 mg of 2-[(1R,2S)-2-{(S)-2-cyclohexylmethoxycarbonylamino-4-methylvalerylamino}-1-hydroxy-3-methylbutyl]-3-phenylcyclopropenone obtained in Example 2 were added 81 mg of acetyl chloride and 102 mg of triethylamine. The resultant mixture was stirred at room temperature for 3 hours, mixed with diluted hydrochloric acid and shaken with methylene chloride. The organic layer was washed with water, saturated aqueous sodium bicarbonate and saturated brine in that order, dried over magnesium sulfate and filtered. The filtrate was concentrated and chromatographed on a column of silica gel, eluting with hexane:ethyl acetate (1:1) to give 73 mg of the titled product. | CC(=O)O[C@H](c1c(-c2ccccc2)c1=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)OCC1CCCCC1)C(C)C | null | CC(C)C[C@H](NC(=O)OCC1CCCCC1)C(=O)N[C@@H](C(C)C)[C@H](O)c1c(-c2ccccc2)c1=O | CC(=O)Cl | null | [CH:1]1([CH2:7][O:8][C:9]([NH:11][C@@H:12]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:13]([NH:15][C@@H:16]([CH:29]([CH3:31])[CH3:30])[C@@H:17]([C:19]2[C:20](=[O:28])[C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:18])=[O:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:36](Cl)(=[O:38])[CH3:37].Cl>C(Cl)Cl.C(N(CC)CC)C>[C:36]([O:18][C@H:17]([C:19]1[C:20](=[O:28])[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][C:9]([O:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:10])[CH2:32][CH:33]([CH3:35])[CH3:34])[CH:29]([CH3:30])[CH3:31])(=[O:38])[CH3:37] | null | ClCCl | CCN(CC)CC | null | null | 45.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
747,806 | [Na+] | [OH-] | null | null | ord_dataset-4b705442211b4a3988e26d5f65098160 | 2006-01-01T00:12:00 | true | 8.26 g (19.5 mmol) of the benzyl ester from example 1 were dissolved in 100 ml THF and stirred overnight with 20 ml 2 M aqueous NaOH. The solvent was removed after filtration, water was added, and the solution extracted with diethyl ether. The aqueous phase was freeze dried and sufficiently pure for further derivatization. | N=C(N)c1ccc(NC(=O)C(C(=O)[O-])c2ccccc2)cc1 | null | N=C(N)c1ccc(NC(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1 | null | null | C([O:8][C:9](=[O:29])[CH:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=1)=[O:12])C1C=CC=CC=1.[OH-].[Na+:31]>C1COCC1>[Na+:31].[C:20]([C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:11](=[O:12])[CH:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:9]([O-:29])=[O:8])=[CH:19][CH:18]=1)(=[NH:21])[NH2:22] | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
454,956 | Cl | [Na+] | [OH-] | null | ord_dataset-4a5b4fffffb34daa876fff1f127a4135 | 2000-01-01T00:01:00 | true | A mixture of Compound B (200 mg, 0.63 mmol), dichloromethane (5 mL), and aqueous sodium hydroxide (1 ml, 1N) was combined and cooled to 0° C. Acetyl chloride (66 mL, 0.94 mmol) was added to the mixture, and after stirring for 2 hour at 0° C. aqueous sodium hydroxide (20 ml, 1N) and dichloromethane (50 mL) were added, followed by extraction with dichloromethane (50 mL). The organic portions were combined, dried (Na2SO4), and concentrated to a crude oil (230 mg, 100%). | CC(=O)N1Cc2cc(Br)ccc2NCC1Cc1ccccc1 | null | CC(=O)Cl | O=C(c1cccc2ccccc12)N1CCN(Cc2c[nH]cn2)c2ccc(Br)cc2C1 | null | Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13]C3N=CNC=3)[CH2:11][CH2:10][N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)C=CC=3)=O)[CH2:8][C:7]=2[CH:31]=1.[OH-].[Na+].C(Cl)(=[O:36])C>ClCCl>[C:10]([N:9]1[CH2:8][C:7]2[CH:31]=[C:3]([Br:2])[CH:4]=[CH:5][C:6]=2[NH:12][CH2:13][CH:19]1[CH2:21][C:30]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:36])[CH3:11] | null | ClCCl | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
80,381 | [K+] | [Na+] | [OH-] | null | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | 1981-01-01T00:04:00 | true | 4-Methylphenacyl bromide (XVI: X=Br) (63 g, 0.296 mole), 4-nitrophenol (XI) (42.4 g, 0.305 mole) and potassium hydroxide (22.5 g, 0.4 mole) were added to methanol (300 ml), and the mixture was heated under reflux for 4 hours. Thereafter, the reaction mixture was treated in the same manner as in Example 29 to obtain 50.0 g of 4-methyl-α-(4-nitrophenoxy)acetophenone (XII) (yield, 62.3%). | CC1([N+](=O)[O-])C=CC(OCC(=O)c2ccccc2)=CC1 | null | Cc1ccc(C(=O)CBr)cc1 | O=[N+]([O-])c1ccc([O-])cc1 | CO | C[C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.O.O.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([O-:23])=[CH:19][CH:18]=1)([O-:16])=[O:15].[Na+].[OH-].[K+].[CH3:27]O>>[CH3:27][C:17]1([N+:14]([O-:16])=[O:15])[CH:22]=[CH:21][C:20]([O:23][CH2:7][C:6]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:11][CH:10]=2)=[O:9])=[CH:19][CH2:18]1 | null | O | null | null | null | 62.3 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
845,204 | [Na+] | null | null | null | ord_dataset-e2b35e721c2741999b0005d12691f9fe | 2008-01-01T00:10:00 | true | Treatment of (±)-[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl 4-methylbenzenesulfonate (1.01 g, 2.56 mmol) with sodium azide (0.664 g, 10.24 mmol) generally according to the procedure described for Intermediate 98 gave (±)-2-(azidomethyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzofuran. Treatment of the azide with palladium on carbon (0.03 g, 10 wt. %) generally according to the procedure described for Example 1 provided 0.528 g (75%) of (±)-1-[7-(4-methylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine as a white solid, hydrochloride salt. mp 231-232° C.; Anal. calcd. for C16H17NOHCl: C, 69.69; H, 6.58; N, 5.08. Found: C, 66.26; H, 7.0; N, 4.73. | Cc1ccc(-c2cccc3c2OC(CN=[N+]=[N-])C3)cc1 | null | Cc1ccc(-c2cccc3c2OC(COS(=O)(=O)c2ccc(C)cc2)C3)cc1 | [N-]=[N+]=[N-] | null | CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[C:21]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)[C:15]=3[O:14]2)(=O)=O)=CC=1.[N-:29]=[N+:30]=[N-:31].[Na+]>>[N:29]([CH2:12][CH:13]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[C:15]=2[O:14]1)=[N+:30]=[N-:31] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,215,314 | [Li+] | null | null | null | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | 2012-01-01T00:10:00 | true | Following general procedure Z3 followed by C, starting from 1-[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-1H-pyrazol-4-ylamine and 5-(6-methyl-pyridin-2-yl)-oxazole-4-carboxylic acid lithium salt. LC-MS-conditions 02: tR=0.75 min; [M+H]+=392.31. | CC(=O)c1ccc(Cn2cc(NC(=O)c3ncoc3-c3cccc(C)n3)cn2)o1 | null | Cc1cccc(-c2ocnc2C(=O)[O-])n1 | CC1(c2ccc(Cn3cc(N)cn3)o2)OCCO1 | null | [CH3:1][C:2]1([C:7]2[O:11][C:10]([CH2:12][N:13]3[CH:17]=[C:16]([NH2:18])[CH:15]=[N:14]3)=[CH:9][CH:8]=2)[O:6]CCO1.[Li+].[CH3:20][C:21]1[N:26]=[C:25]([C:27]2[O:31][CH:30]=[N:29][C:28]=2[C:32]([O-])=[O:33])[CH:24]=[CH:23][CH:22]=1>>[C:2]([C:7]1[O:11][C:10]([CH2:12][N:13]2[CH:17]=[C:16]([NH:18][C:32]([C:28]3[N:29]=[CH:30][O:31][C:27]=3[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:20])[N:26]=3)=[O:33])[CH:15]=[N:14]2)=[CH:9][CH:8]=1)(=[O:6])[CH3:1] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,708,537 | CCCC[N+](CCCC)(CCCC)CCCC | [F-] | [Li+] | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | (5R,6S)-1-((S)-1-(Tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-ethylpiperidin-2-one (421 mg, 0.639 mmol; Example 202, Step A) was azeotroped with toluene (3×). THF (1.6 mL) was added. The mixture was sparged with argon for 5 minutes and then cooled to 0° C. 1.0 M lithium diisopropylamide solution in THF (1.246 mL, 1.246 mmol) was added dropwise. After 25 minutes, allyl bromide (0.166 mL, 1.917 mmol) was added dropwise. After 20 minutes, the mixture was quenched with sat. aq. NH4Cl solution. The mixture was extracted with ethyl acetate. The organic layer was washed with sat. aq. NaCl solution, dried over Na2SO4, and concentrated. The residue was dissolved in THF (3 mL) and 1.0M tetrabutylammonium fluoride solution in THF (2.335 mL, 2.335 mmol) was added. After stirring overnight, the mixture was partitioned between 5% aq. HCl and ethyl acetate. The organic layer was washed with sat. aq. NaCl solution, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (eluent: 20 to 50% ethyl acetate/hexanes) to afford the title compound as the more polar major diastereomer. | C=CCC1(CC)C[C@H](c2cccc(Cl)c2)[C@@H](c2ccc(Cl)cc2)N([C@@H](CC)CO)C1=O | null | CC(C)[N-]C(C)C | CCC1C[C@H](c2cccc(Cl)c2)[C@@H](c2ccc(Cl)cc2)N([C@@H](CC)CO[Si](c2ccccc2)(c2ccccc2)C(C)(C)C)C1=O | null | [Si]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][CH:25]([CH2:43][CH3:44])[C:24]1=[O:45])[CH2:21][CH3:22])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:46]([N-]C(C)C)([CH3:48])[CH3:47].[Li+].C(Br)C=C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C1(C)C=CC=CC=1>[CH2:48]([C:25]1([CH2:43][CH3:44])[CH2:26][C@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[C@@H:28]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[N:23]([C@@H:20]([CH2:21][CH3:22])[CH2:19][OH:18])[C:24]1=[O:45])[CH:46]=[CH2:47] | 0.42 | C1CCOC1 | Cc1ccccc1 | C=CCBr | 0 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
535,384 | [BH3-]C#N | [Na+] | null | null | ord_dataset-1884c7bf3d544afdb8d17b5d41b90a27 | 2002-01-01T00:03:00 | true | To a solution of 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.7 g) in methanol (7 ml) were added benzaldehyde (229 mg) and acetic acid (130 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano-borohydride (135 mg). The mixture was stirred for 30 minutes at room temperature, to which was added ethyl acetate ester (50 ml). The mixture was washed with water and dried over anhydrous MgSO4, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography to give the object 2-benzylamino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.91 g) as a colorless oily compound. | CC(C)(C)OC(=O)NCc1cccc(C(O)c2cc(Cl)ccc2NCc2ccccc2)c1 | null | CC(C)(C)OC(=O)NCc1cccc(C(O)c2cc(Cl)ccc2N)c1 | O=Cc1ccccc1 | null | [NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=1.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH2:26]([NH:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:20])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH:6]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1 | 0.17 | CO | CCOC(C)=O | CC(=O)O | 25 | null | 104.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,567,731 | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | ord_dataset-9741bb5fd93044078df2a45f45733054 | 2015-01-01T00:04:00 | true | To a mixture of tert-butyl piperazine-1-carboxylate (1.81 g, 9.7 mmol), 3-fluoro-4-methylbenzoic acid (1.50 g, 9.7 mmol), and triethylamine (6.8 mL, 49 mmol) in acetnitrile (30 mL), HBTU (4.06 g, 10.7 mmol) was added. After stirring at rt for 1 h, the mixture was poured onto water (150 mL), and the mixture was extracted with EtOAc (twice). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (4:1-2:1) to give 3.14 g (quant) of the title compound as a white solid. | Cc1ccc(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)cc1F | null | Cc1ccc(C(=O)O)cc1F | CC(C)(C)OC(=O)N1CCNCC1 | null | [N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18](O)=[O:19].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[O:19] | 1 | CC#N | CCN(CC)CC | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,225,838 | null | null | null | null | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | 2012-01-01T00:11:00 | true | To 4-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole (3.95 g, 7.95 mmol) is added acetonitrile (300 mL). To this solution is added 3-bromo-4-bromomethylbenzonitrile (2.14 g, 7.78 mmol). The solution is stirred at 40° C. for 18 h. The solvent is then removed in vacuo and methanol (300 ml) is added. The solution is heated to 55° C. and stirred for 1.5 h. Saturated sodium bicarbonate is then added and stirred for 10 min. The organic solvent is removed in vacuo, and the crude product extracted into ethyl acetate and washed with water. The organic solvent is removed in vacuo to give the crude product. Chromatography (silica gel, 1:0 to 1:1 to 0:1 hexanes:ethyl acetate) gives the pure product. MS (ESI) m/z 448, 450 (M+H). | CC(C)(C)[Si](C)(C)OCCCCc1cn(Cc2ccc(C#N)cc2Br)cn1 | null | CC(C)(C)[Si](C)(C)OCCCCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | N#Cc1ccc(CBr)c(Br)c1 | null | [Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(#N)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49]Br)[C:44]#[N:45]>C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49][N:16]1[CH:17]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:14]=[CH:15]1)[C:44]#[N:45] | 18 | CCOC(C)=O | CC#N | null | 40 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
493,560 | null | null | null | null | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | 2001-01-01T00:02:00 | true | In an analogous manner to that described in Example 5, from 7-chloro-5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl) -pyrazolo[1,5-a]pyrimidine and dimethylamine in EtOH there was obtained dimethyl-[5-methyl-2-methylsulphanyl-3-(toluene-4-sulphonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-amine as colorless crystals, m.p. >230°. | CSc1nn2c(N(C)C)cc(C)nc2c1S(=O)(=O)c1ccc(C)cc1 | null | CSc1nn2c(Cl)cc(C)nc2c1S(=O)(=O)c1ccc(C)cc1 | CNC | null | Cl[C:2]1[N:7]2[N:8]=[C:9]([S:21][CH3:22])[C:10]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[C:6]2[N:5]=[C:4]([CH3:23])[CH:3]=1.[CH3:24][NH:25][CH3:26]>CCO>[CH3:24][N:25]([CH3:26])[C:2]1[N:7]2[N:8]=[C:9]([S:21][CH3:22])[C:10]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[C:6]2[N:5]=[C:4]([CH3:23])[CH:3]=1 | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
419,878 | On1nnc2ccccc21 | null | null | null | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | 1998-01-01T00:12:00 | true | With the exclusion of air, 270 mg (1.43 mmol) of N-methoxycarbonyl-(L)-iso-leucine, 513 mg (2.67 mmol) of EDC and 241 mg (1.78 mmol) of HOBT are dissolved in 7.8 ml of DMF. After stirring for 15 min, 0.75 ml (5.4 mmol) of TEA and 510 mg (0.89 mmol) of 1-{4-[2-(1-methyl -1-phenyl-ethyl)-2H-tetrazol-5-yl]-phenyl}-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane (Example 25f) in 3.7 ml of DMF are added. After 20 hours, the mixture is worked up analogously to Example 25g to yield the title compound: HPLC20-100 : tRet =18.5; FAB MS (M+H)+ =743. | CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2nnn(C(C)(C)c3ccccc3)n2)cc1)NC(=O)OC(C)(C)C | null | CC[C@H](C)[C@H](NC(=O)OC)C(=O)O | CC(C)(C)OC(=O)NN(Cc1ccc(-c2nnn(C(C)(C)c3ccccc3)n2)cc1)C[C@H](O)[C@@H](N)Cc1ccccc1 | null | [CH3:1][O:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[C@H:7]([CH2:9][CH3:10])[CH3:8])=[O:4].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:28][C:29]([N:37]1[N:41]=[N:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([CH2:48][N:49]([NH:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:50][C@H:51]([OH:61])[C@@H:52]([NH2:60])[CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:44][CH:43]=2)=[N:38]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:30]>CN(C=O)C>[CH3:30][C:29]([N:37]1[N:41]=[N:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([CH2:48][N:49]([NH:62][C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:50][C@H:51]([OH:61])[C@@H:52]([NH:60][C:11](=[O:13])[C@H:6]([C@H:7]([CH2:9][CH3:10])[CH3:8])[NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[CH:44][CH:43]=2)=[N:38]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:28] | 0.25 | ClCCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
914,550 | CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C | CN(C1CCCCC1)C1CCCCC1 | null | null | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | 2009-01-01T00:10:00 | true | A solution of 10.0 g (51.0 mmol) of 4-bromo-2-methylbenzonitrile in 80 mL of 1,4-dioxane was treated with 7.19 g (56.1 mmol) of tert-butyl acrylate, 10.96 g (56.1 mol) of N-methyldicyclohexylamine, 228 mg (0.76 mol) of 2-(di-tert-butylphosphino) biphenyl, and 396 mg (0.38 mol) of tris(dibenzylideneacetone)dipalladium(0)-chloroforin adduct. The resulting mixture was heated at 70° C. for 16 h and cooled to rt. The reaction mixture was filtered though a filter paper, and the filtrate was concentrated. The crude product was partitioned into four portions. Chromatography on four Biotage 40M cartridges using 19:1 v/v hexanes/EtOAc as the eluant followed by pooling of product fractions afforded 10.0 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.55 (s, 9H), 2.58 (s, 3H), 6.44 (d, J=16.0, 1H), 7.41 (d, J=8.0, 1H), 7.45 (s, 1H), 7.53 (d, J=16.0, 1H), 7.61 (d, J=8.0, 1H). | Cc1cc(C=CC(=O)OC(C)(C)C)ccc1C#N | null | C=CC(=O)OC(C)(C)C | Cc1cc(Br)ccc1C#N | null | Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[CH:12]=[CH2:13].CN(C1CCCCC1)C1CCCCC1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH3:10][C:4]1[CH:3]=[C:2]([CH:13]=[CH:12][C:11]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7] | null | C1COCCO1 | null | null | 70 | null | 80.6 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,696,816 | null | null | null | null | ord_dataset-54347fcace774f89850681d6dec8009f | 2016-01-01T00:03:00 | true | The title compound or its salt was prepared by a procedure similar to that described for E59 starting from (2,3-difluorophenyl)methanamine and 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one. | CN1CCCn2c1cc(NCc1cccc(F)c1F)nc2=O | null | CN1CCCn2c1cc(Cl)nc2=O | NCc1cccc(F)c1F | null | [F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][NH2:10].Cl[C:12]1[CH:22]=[C:16]2[N:17]([CH3:21])[CH2:18][CH2:19][CH2:20][N:15]2[C:14](=[O:23])[N:13]=1>>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:12]1[CH:22]=[C:16]2[N:17]([CH3:21])[CH2:18][CH2:19][CH2:20][N:15]2[C:14](=[O:23])[N:13]=1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
107,824 | null | null | null | null | ord_dataset-29d79fca4cec4a43b773d0ba25b27651 | 1983-01-01T00:08:00 | true | To a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-imidazolyl)carbonyloxymethyl-3-cephem-4-carboxylate (syn isomer) (13.5 g) in tetrahydrofuran (200 ml) was added m-chloroperbenzoic acid (5.8 g) with stirring under ice-cooling, followed by stirring for an hour at 5° C. The reaction mixture was evaporated and the residue was pulverized in diethyl ether, collected by filtration, washed with ethyl acetate and diethyl ether and then dried to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-imidazolyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (11.0 g). | CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(COC(=O)n3ccnc3)CS(=O)[C@H]12)c1csc(NC=O)n1 | null | O=C(OO)c1cccc(Cl)c1 | CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(COC(=O)n3ccnc3)CS[C@H]12)c1csc(NC=O)n1 | null | [CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)=[O:18])[CH2:13][S:14][C@H:9]12)=[O:6].ClC1C=CC=C(C(OO)=[O:58])C=1>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:5]([NH:7][CH:8]1[C:40](=[O:41])[N:10]2[C:11]([C:24]([O:26][CH:27]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:12]([CH2:15][O:16][C:17]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)=[O:18])[CH2:13][S:14](=[O:58])[C@H:9]12)=[O:6] | null | C1CCOC1 | null | null | null | 79.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
296,717 | CCCC[N+](CCCC)(CCCC)CCCC | Cl | [F-] | null | ord_dataset-ec7cb3d5a8704f64b01d401ea555974f | 1994-01-01T00:09:00 | true | The 1-[3-[(1,1-dimethylethyl)dimethylsiloxy]phenyl]-2-[(dimethylamino)methylene]-2-(4,5-diphenyl-2-oxazolyl)ethanone (19) (10.3 g, 19.6 mmol) was dissolved in THF (100 mL) and tetra-n-butyl ammonium fluoride (17.5 mL of 1M in THF) was added dropwise. The reaction mixture was stirred for about 1/4 hour and poured onto an ether (180 mL)/1N HCl(20 mL) solution, and the organic phase separated and dried (MgSO4). Chromatography (elution with 75% ethyl acetate/hexanes) gave the phenol 7.7 g (96%). IR (KBr, cm-1) 3170, 3060, 2920, 1735, 1635, 1600, 1447, 1375, 1310, 1210, 1010, 965, 870, 765, 695. 1H NMR (300 MHz, CDCl3) δ 2.6 to 3.1 (6H, Series of Br. s) 6.84 (1H, Br.s), 6.95 (1H, Br. s), 7.04 to 7.24 (10H, m), 7.32 to 7.60 (5H, m). m/e 411 (MH+) | CN(C)C=C(C(=O)c1cccc(O)c1)c1nc(-c2ccccc2)c(-c2ccccc2)o1 | null | CN(C)C=C(C(=O)c1cccc(O[Si](C)(C)C(C)(C)C)c1)c1nc(-c2ccccc2)c(-c2ccccc2)o1 | null | null | CC([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:36])[C:14](=[CH:32][N:33]([CH3:35])[CH3:34])[C:15]2[O:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH:10]=[CH:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.Cl>C1COCC1>[OH:6][C:7]1[CH:8]=[C:9]([C:13](=[O:36])[C:14](=[CH:32][N:33]([CH3:35])[CH3:34])[C:15]2[O:16][C:17]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH:10]=[CH:11][CH:12]=1 | null | C1CCOC1 | CCOCC | null | null | null | 95.7 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,003,677 | [Pd+2] | [OH-] | null | null | ord_dataset-70899a0178cc441482746c093624afa0 | 2010-01-01T00:10:00 | true | A mixture of 4-benzyloxycarbonyl-1-(4-fluorobenzyl)-3,4-dihydro-pyrazin-2(1H)-one (0.5 g, 1.45 mmol) and Pearlman's catalyst (26 mg; 20% palladium hydroxide on carbon) in methanol (25 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature overnight. The product mixture was filtered through a pad of Celite, and concentrated under vacuum to provide 1-(4-fluorobenzyl)piperazin-2-one. 1H NMR (400 MHz, d6 DMSO) δ 7.29 (dd, J=8.4, 5.7 Hz, 2H), 7.16 (t, J=9.0 Hz, 2H), 4.48 (s, 2H), 3.28 (s, 2H), 3.14 (t, J=5.3 Hz, 2H) 2.84 (t, J=5.3 Hz, 2H); ES MS (M+1)=209. | O=C1CNCCN1Cc1ccc(F)cc1 | null | O=C1CN(C(=O)OCc2ccccc2)C=CN1Cc1ccc(F)cc1 | null | null | C(OC([N:11]1[CH:16]=[CH:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:13](=[O:25])[CH2:12]1)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:14]2[CH2:15][CH2:16][NH:11][CH2:12][C:13]2=[O:25])=[CH:19][CH:20]=1 | 8 | CO | null | null | 25 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
533,508 | CCCC[N+](CCCC)(CCCC)CCCC | O=S(=O)([O-])O | [K+] | null | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | 2002-01-01T00:02:00 | true | A solution of potassium peroxymonosulfate (4.1 g) in water (21 ml) was added dropwise to a mixture of ethyl 2,3-dihydro-7-methylthio-1-benzoxepin-4-carboxylate (0.8 g) and tetrabutylammonium hydrogen sulfate (0.2 g) in ethyl acetate (8 ml) and water (4 ml) at ambient temperature and the mixture was stirred at the same temperature for 3 hours. The separated organic layer was washed with 10% aqueous sodium thiosulfate. The organic layer was washed with water, dried over magnesium sulfate and evaporated in vacuo to give ethyl 2,3-dihydro-7-methanesulfonyl-1-benzoxepin-4-carboxylate (0.77 g). | CCOC(=O)C1=Cc2cc(S(C)(=O)=O)ccc2OCC1 | null | O=S(=O)([O-])O[O-] | O | CCOC(=O)C1=Cc2cc(SC)ccc2OCC1 | S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][S:10][C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=2[CH:26]=1.[OH2:27]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:9][S:10]([C:11]1[CH:12]=[CH:13][C:14]2[O:20][CH2:19][CH2:18][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=2[CH:26]=1)(=[O:2])=[O:27] | 3 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
245,973 | Cl | null | null | null | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | 1992-01-01T00:04:00 | true | To a dispersion of 1.51 g of 2-mercaptoimidazo[4,5-b]pyridine in 25 ml of ethanol was added at once 1.92 g of 2-(methylamino)benzyl chloride hydrochloride at room temperature under stirring. The resulting mixture was further stirred for 3.5 hours. The precipitated crystals were collected by filtration and washed with ethanol. The obtained crystals were added portionwise to a mixture of 100 ml of chloroform and 100 ml of 1N NaOH solution for neutralization. The aqueous NaOH phase was separated, and to this phase were successively added 200 ml of chloroform and a saturated ammonium chloride solution until the aqueous phase showed no turbidity upon addition of the solution. The chloroform phase was separated, washed with a saturated aqueous sodium chloride solution, and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was crystallized by addition of diethyl ether. The crystalline product was collected by filtration and dried to give 1.84 g (yield: 68.1%) of 2-[2-(methylamino)benzylthio]imidazo[4,5-b]pyridine as a white crystalline powder. | CNc1ccccc1CSc1nc2ncccc2[nH]1 | null | CNc1ccccc1CCl | Sc1nc2ncccc2[nH]1 | null | [SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.Cl.[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl>C(O)C>[CH3:12][NH:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][S:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2 | null | CCO | null | null | null | 68.1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,092,854 | null | null | null | null | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | 2011-01-01T00:09:00 | true | Ethoxycarbonyl isothiocyanate (0.5 ml, 4.18 mmol) was added to a solution of 4-[(quinolin-4-ylmethyl)amino]-1H-imidazole-4-carboxamide (0.93 g, crude material from Example 24(a)) dissolved in anhydrous dichloromethane (10 mL) and methanol (5 mL) mixture. After o.n. (over night) at r.t., the solution was concentrated in vacuo and the residue was dissolved in 1N NaOH solution (30 mL) and refluxed for 3.5 h. After cooling to r.t., the pH was adjusted to ˜6.5 with 2 N HCl. The solid that formed was collected by filtration and dried generating 0.35 g of crude material. A portion of the solid (150 mg) was purified by preparative HPLC, and the solid obtained was washed with dichloromethane and ether, generating 25.9 mg (9% yield over two steps) of the title compound. | O=c1[nH]c(=S)n(Cc2ccnc3ccccc23)c2nc[nH]c12 | null | CCOC(=O)N=C=S | NC(=O)C1(NCc2ccnc3ccccc23)CNC=N1 | null | C(O[C:4]([N:6]=[C:7]=[S:8])=[O:5])C.[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][NH:20][C:21]2(C(N)=O)[CH2:25][NH:24][CH:23]=[N:22]2)=[CH:11][CH:10]=1.CO>ClCCl>[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][N:20]2[C:21]3[N:22]=[CH:23][NH:24][C:25]=3[C:4](=[O:5])[NH:6][C:7]2=[S:8])=[CH:11][CH:10]=1 | null | CO | ClCCl | null | 25 | 9 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
1,496,232 | null | null | null | null | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | 2014-01-01T00:10:00 | true | The title compound was prepared by a procedure similar to that described for E1 starting from 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-{[(2-oxo-2,3-dihydro-4-pyrimidinyl)oxy]methyl}benzonitrile and bromoethane. LC-MS (ESI): m/z 450 [M+H]+; 4.11 min (ret time). | CCn1ccc(OCc2ccc(Oc3ccc(Cl)c(C(F)(F)F)c3)c(C#N)c2)nc1=O | null | CCBr | N#Cc1cc(COc2ccnc(=O)[nH]2)ccc1Oc1ccc(Cl)c(C(F)(F)F)c1 | null | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[NH:20][C:21](=[O:25])[N:22]=[CH:23][CH:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].Br[CH2:31][CH3:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][N:22]([CH2:31][CH3:32])[C:21](=[O:25])[N:20]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:26]([F:27])([F:29])[F:28] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null |
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