original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | 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_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 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 | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
817,496 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | COC1C=CC(C[N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11]([Cl:18])=[C:10]([C:19]#[N:20])[C:9]2=[O:21])=CC=1>C(O)(C(F)(F)F)=O>[Cl:18][C:11]1[C:12]2[C:17](=[N:16][CH:15]=[CH:14][CH:13]=2)[NH:8][C:9](=[O:21])[C:10]=1[C:19]#[N:20] | COc1ccc(Cn2c(=O)c(C#N)c(Cl)c3cccnc32)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(4-methoxybenzyl)-4-chloro-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carbonitrile (32) (326 mg, 1 mmol) in TFA was refluxed for 24 h. The solution was cooled and excess TFA was distilled off under reduced pressure. The residue was taken in water, basified by solid NaHCO3 and filtered. The solids were washed... | N#Cc1c(Cl)c2cccnc2[nH]c1=O | null | 95.8 | null |
15,592 | ord_dataset-b971427c0b944c56b63bb2356fa8ca69 | null | 1976-01-01T00:11:00 | true | C[Si](C)(C)[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[NH2:10][C:11](N)=[O:12].[Cl-].[NH4+].N>C1(C)C=CC=CC=1>[CH3:5][Si:4]([NH:10][C:11](=[O:12])[NH:3][Si:4]([CH3:5])([CH3:6])[CH3:7])([CH3:7])[CH3:6] | C[Si](C)(C)N[Si](C)(C)C | NC(N)=O | null | N | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 110 | null | A mixture containing 750 parts by volume of hexamethyldisilazane, 750 parts by volume of toluene, 180 parts urea and 0.5 part of ammonium chloride is heated to reflux temperature (approx. 110° C.). After refluxing for 1.25 hours the evolution of ammonia has stopped and the reaction is considered to be complete. The pro... | C[Si](C)(C)NC(=O)N[Si](C)(C)C | null | 98.4 | null |
1,709,520 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | Cl[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[CH2:6][CH2:5]1.[OH:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22]([O:28][CH2:29][CH3:30])=[N:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH3:16][C:13]1[N:12]=[N:11][C:10]([N:7]2[CH2:8][CH2:9]... | Cc1ccc(N2CCC(CCCl)CC2)nn1 | CCOc1ncnc2cc(O)ccc12 | null | O=C([O-])[O-] | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 90 | null | A mixture of 3-[4-(2-chloroethyl)-1-piperidinyl]-6-methylpyridazine (76 mg, 318 μmol), 7-hydroxy-4-ethoxyquinazoline (100 mg, 526 mmol), potassium carbonate (109 mg, 789 mmol) and potassium iodide (53 mg, 319 mmol) in DMF (5 mL) was heated at 90° C. overnight in an argon atmosphere. The mixture was concentrated, and th... | CCOc1ncnc2cc(OCCC3CCN(c4ccc(C)nn4)CC3)ccc12 | null | 17.6 | null |
216,354 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | C[O:2][CH:3](OC)[CH2:4][CH2:5][C:6]([O:9][CH3:10])([CH3:8])[CH3:7].O1CCCC1.C(O)(=O)C(O)=O>O>[CH3:10][O:9][C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][CH:3]=[O:2] | COC(CCC(C)(C)OC)OC | null | null | O=C(O)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 1,1,4-trimethoxy-4-methylpentane (3.2 g, 0.018 mol), tetrahydrofuran (100 mL), water (10 mL) and oxalic acid (1.0 g, 0.022 mol) was heated at reflux for 40 hours. Workup provided 4-methoxy-4-methylpentanal (2.0 g). | COC(C)(C)CCC=O | null | 85.3 | null |
1,413,382 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1>>[F:9][C:7]1[CH:8]=[C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([O:11][CH3:10])[CH:17]=2)[CH:3]=[CH:4][C:5]=1[NH2:6] | Nc1ccc(Br)cc1F | COc1cccc(B(O)O)c1 | 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 | null | null | The title compound (430 mg) was prepared from 4-bromo-6-fluoroaniline (500 mg, 2.63 mmol) and 3-Methoxyphenylboronic acid (519 mg, 3.42 mmol) as a red liquid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.34 (dd, J 2, 13.1, 1H), 7.27 (t, J 7.9, 1H), 7.22 (dd, J 2, 8.3, 1H), 7.12 (d, J 7.9, 1H), 7.09-7.07 (m, 1H), 6.84-6.78 (m, 2... | COc1cccc(-c2ccc(N)c(F)c2)c1 | null | 75.3 | null |
843,294 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | Br[CH2:2][C:3]([CH2:26][CH3:27])=[CH:4][CH2:5][C:6]1[C:14]([O:15]CC[Si](C)(C)C)=[C:13]2[C:9]([CH2:10][O:11][C:12]2=[O:22])=[C:8]([CH3:23])[C:7]=1[O:24][CH3:25].C[O:29][P:30]([O:33]C)[O:31]C.C[Si](Br)(C)C.N1C(C)=CC=CC=1C>>[CH2:26]([C:3](=[CH:4][CH2:5][C:6]1[C:14]([OH:15])=[C:13]2[C:9](=[C:8]([CH3:23])[C:7]=1[O:24][CH3:2... | COP(OC)OC | CCC(=CCc1c(OC)c(C)c2c(c1OCC[Si](C)(C)C)C(=O)OC2)CBr | null | C[Si](C)(C)Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1cccc(C)n1 | null | null | null | null | null | null | null | null | null | null | 25 | 4 | A solution of 6-(3-bromomethyl-pent-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (230 mg, 0.5 mmol) in trimethylphosphite (1.5 mL, 12.75 mmol) was heated to 100° C. for 4 hours. The reaction was worked up by removal of excess trimethylphosphite under reduced pressure. The residue was ... | CCC(=CCc1c(O)c2c(c(C)c1OC)COC2=O)CP(=O)(O)O | null | 43.2 | null |
1,281,941 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]1([C@@H:7]([NH:14][C:15]([C@H:17]2[N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19][S:18]2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>>[C:29]1([C:39]2[CH:44]=[C... | O=S(=O)(Cl)c1ccc(-c2ccccc2)cc1 | CC(C)(C)OC(=O)N1CCS[C@H]1C(=O)N[C@H](c1ccccc1)c1ccccn1 | 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 | null | null | Following the general strategies and protocols outlined in Example 1, starting from tert-butyl (2S)-2-({[(R)-phenyl(pyridin-2-yl)methyl]amino}-carbonyl)-1,3-thiazolidine-3-carboxylate (Intermediate 6) and [1,1′-biphenyl]-4-sulfonyl chloride, the title compound was obtained in 99% purity by HPLC. | O=C(N[C@H](c1ccccc1)c1ccccn1)[C@@H]1SCCN1S(=O)(=O)c1ccc(-c2ccccc2)cc1 | null | null | null |
1,546,177 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:23]=[CH:22][C:15]4[N:16]=[C:17](S(C)=O)[S:18][C:14]=4[CH:13]=3)[C:5]2=[N:6][CH:7]=1.[NH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[F:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH2:11][C:12]3[CH:23]=[CH:22][C:15... | N[C@H]1CC[C@H](O)CC1 | CS(=O)c1nc2ccc(Cn3cnc4cc(F)cnc43)cc2s1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 110 | null | To a stirred suspension of 6-((6-fluoro-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (119 g, 0.3 mmol) from Step 4 of Example 162 and trans-4-aminocyclohexanol (119 mg, 1.0 mmol) in anhydrous DMA (1 mL) was added DIEA (180 μL, 1.0 mmol). The mixture was heated in a sealed tube at 110° C. for... | O[C@H]1CC[C@H](Nc2nc3ccc(Cn4cnc5cc(F)cnc54)cc3s2)CC1 | null | null | null |
171,133 | ord_dataset-41558b7e18dd41999311b1762e0e13a3 | null | 1988-01-01T00:04:00 | true | [CH:1]1(CCCCCCCCCCCCN)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:25]([N:39]=[C:40]=[O:41])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[CH:1]1([N:39]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]... | CCCCCCCCCCCCCCN=C=O | NCCCCCCCCCCCCC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O | 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 | null | null | The preparation is analogous to Example 42, starting from 7.0 g of the compound of Example 1 and 4.8 g of tetradecyl isocyanate. | CCCCCCCCCCCCCCNC(=O)N(CCCCCCCCCCCC)C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O | null | null | null |
1,537,575 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[CH2:11]1[CH2:20][O:19][C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][N:16]1[CH2:17][CH2:18][C:13]2([O:19][CH2:20][CH2:11][O:12]2)[CH2:... | C1CC2(CCN1)OCCO2 | O=Cc1ccc(F)c(F)c1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(Cl)Cl | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3,4-difluorobenzaldehyde (4.40 g, 30.9 mmol), 4,4-ethylenedioxy-piperidine (4.40 g, 30.9 mmol), sodium triacetoxyborohydride (6.40 g, 30.2 mmol) and acetic acid (1.8 g, 30.0 mmol) in dichloroethane (200 ml) was stirred at room temperature for 18 h. After this period, the reaction mixture was washed with 1... | Fc1ccc(CN2CCC3(CC2)OCCO3)cc1F | null | 94.9 | null |
1,504,181 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:21][C@H:22]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:23]([NH2:25])=[O:24])=[N:7][C:8]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:20][N:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)#[N:2].[OH-].[Na+].OO.CC(O)=[O:36]>CCO.CS(C)=O>[NH2:25][C:23](=[O:24])[C@H:22]([NH:21][C:6]1[N:7]=[C:8]([NH:9][C:... | CC(=O)O | CC(C)C[C@@H](Nc1cnc(C#N)c(Nc2ccc(-c3ccno3)cc2)n1)C(N)=O | null | OO | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CCO | null | null | null | null | null | null | null | null | null | 25 | 0.5 | The compound (R)-2-(5-cyano-6-(4-(isoxazol-5-yl)phenylamino)pyrazin-2-ylamino)-4-methylpentanamide (5 mg, 0.012 mmol) was dissolved in EtOH (1 mL) and DMSO (0.5 mL), aq. 1N NaOH (0.50 mL) and aq. H2O2 (30%, 0.50 mL) were added. The mixture was stirred at room temperature for 30 min. HOAc (0.2 mL) was added. The mixture... | CC(C)C[C@@H](Nc1cnc(C(N)=O)c(Nc2ccc(-c3ccno3)cc2)n1)C(N)=O | null | null | null |
1,158,188 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4]/[N:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[NH:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].[SH:22][C@@H:23]([CH2:27][C:28]([OH:30])=[O:29])[C:24](O)=[O:25]>C1(C)C=CC=CC=1>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][NH:14][C:8]1[C:9]([F:13])=[CH:10][CH:11]=[... | CN(C)CCNc1c(F)cccc1/C=N/CCC(C)(C)C | O=C(O)C[C@H](S)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | 2-((E)-(3,3-dimethylbutylimino)methyl)-N-(2-(dimethylamino)ethyl)-6-fluorobenzenamine (175 mg, 0.5964 mmol) and (S)-2-mercaptosuccinic acid (102 mg, 0.6793 mmol) were stirred in toluene (7 mL) at 80° C. for 24 hours. Crude 2-(2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl... | CN(C)CCNc1c(F)cccc1C1SC(CC(=O)O)C(=O)N1CCC(C)(C)C | null | null | null |
559,421 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:14]=1[CH3:20]>>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:17]2[CH:16]=[CH:15][C:14]([CH3:20])=[C:13]([Cl:12])[CH:18]=2)[CH:3]=1 | Clc1ccnc2ccccc12 | Cc1ccc(I)cc1Cl | 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 | null | null | The title compound, m. p. 115-116° C., MS: m/e=288 (M+), was prepared from 4-chloroquinoline and 2-chloro-4-iodo-toluene. | Cc1ccc(-c2cc(Cl)c3ccccc3n2)cc1Cl | null | null | null |
738,422 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [H-].[Na+].Cl.[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].[CH3:16][O:17][CH2:18][CH2:19]Br>CN(C=O)C.CCOC(C)=O>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:19][CH2:18][O:17][CH3:16])[C:6]1=[O:15] | NC1Cc2ccccc2NC1=O | COCCBr | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | Sodium hydride (60% in oil, 321 mg, 8.03 mmol) was added to 3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride (J. Med. Chem., 28, 1985; 1511–16; 759 mg, 3.82 mmol) in anhydrous DMF (10 mL) at 0° C. over a period of 5 min. After 1 hour 2-bromoethyl methyl ether (0.40 mL, 4.20 mmol) was added and stirring maintained fo... | COCCN1C(=O)C(N)Cc2ccccc21 | null | 77.7 | null |
148,600 | ord_dataset-0b70410902ae4139bd5d334881938f69 | null | 1986-01-01T00:09:00 | true | [C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[Si:7]([CH2:14][CH2:15][SH:16])([O:12][CH3:13])([O:10][CH3:11])[O:8][CH3:9].[OH-].[K+]>O>[Si:7]([CH2:14][CH2:15][S:16][CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])([O:12][CH3:13])([O:10][CH3:11])[O:8][CH3:9] | C=CC(=O)OC | CO[Si](CCS)(OC)OC | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 60 | null | A mixture of 26 gms of methyl acrylate (0.3 mols) and 36.4 gms of (CH3O)3SiCH2CH2SH was catalyzed by adding 1 ml. of N/2 alcoholic KOH into a 250 ml., round bottomed glass flask, with stirring. An exothermic reaction raised the temperature to 60° C. The mixture was refluxed for 30 minutes and then distilled under vacuu... | COC(=O)CCSCC[Si](OC)(OC)OC | null | 87 | null |
178,337 | ord_dataset-4d84abdf99524e0fb6c42ab2a3300790 | null | 1988-01-01T00:10:00 | true | [Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]3C=C[N:20]=[CH:19]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:27](=NO)(N)[CH2:28][CH2:29][CH2:30]C>CN(C)C=O>[CH2:27]([C:19]1[N:18]=[C:16]([C:15]2[N:14]=[CH:13][N:12]3[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([Cl:... | CCCCC(N)=NO | O=C1c2c(Cl)cccc2-n2cnc(C(=O)n3ccnc3)c2[C@@H]2CCCN12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 2 | 11.0 g (30 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 50 ml of N,N-dimethylformamide, whereupon the solution is treated with 3.96 g (34 mmol) of valeramidoxime and the mixture is heated to 85° for 3 hours. The reacti... | CCCCc1noc(-c2ncn3c2[C@@H]2CCCN2C(=O)c2c(Cl)cccc2-3)n1 | null | null | null |
1,096,371 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15]>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH3:15] | CCCCOc1cc(C(=O)O)ccc1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 65 | 8 | A solution of 20.1 (0.68 g, 2490 μmol) in THF (5 mL) was treated with borane THF complex (4979 μL, 4979 μmol) and stirred overnight at 65° C. The reaction mixture was quenched with MeOH, diluted with EtOAc, and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was ... | CCCCOc1cc(CO)ccc1Br | null | 102.2 | null |
290,027 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[C:34](O)=[O:35].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C>>[CH2:... | O=C(O)c1cc2ccccc2[nH]1 | N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1 | null | O=C1OCCN1P(=O)(Cl)N1CCOC1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | 200 mg (0.550 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 4a with 106 mg (0.661 mmol) of indole-2-carboxylic acid, 168 mg (0.661 mmol) of bis(2-oxo-3-oxazolidinyl)phosphinic chloride and 169 μl (1.21 mmol) of triethylamine. The title compound ##STR87## is obtai... | O=C(N[C@H]1CCN(C(=O)c2cc(Cl)cc(Cl)c2)[C@H](Cc2ccccc2)C1)c1cc2ccccc2[nH]1 | null | null | null |
1,077,332 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.[S-:10][C:11]#[N:12].[K+]>O>[NH:12]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:3]=2[N:2]=[C:11]1[SH:10] | NC1CCCCC1=O | N#C[S-] | null | Cl | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 100 | 16 | Dissolve 2-amino-cyclohexanone hydrochloride (2.2 g, 14.7 mmol) and potassium thiocyanate (1.4 g, 14.7 mmol) in water (10 mL). Stir the solution at 100° C. in a sealed flask for 16 h. Cool the mixture and store the mixture at 4° C. for 16 h. Filter off the resulting solid and wash with water (20 mL). Collect the solid,... | Sc1nc2c([nH]1)CCCC2 | null | 61.7 | null |
916,474 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | [NH2:1][C:2]1[C:7]([C:8]#[C:9][CH2:10][OH:11])=[N:6][C:5]([S:12][CH3:13])=[CH:4][N:3]=1>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH3:13][S:12][C:5]1[N:6]=[C:7]2[CH:8]=[C:9]([CH:10]=[O:11])[NH:1][C:2]2=[N:3][CH:4]=1 | CSc1cnc(N)c(C#CCO)n1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 7.5 | 1 | To a solution of the compound obtained in Example 34 (4) (123 mg) in acetone (40 ml), manganese dioxide (1.86 g) was added and the mixture was stirred at −15 to 30° C. for-1 hour. The reaction solution was filtered through Celite and concentrated under reduced pressure to obtain 60 mg (49.3%) of the desired product as ... | CSc1cnc2[nH]c(C=O)cc2n1 | null | 49.3 | null |
286,189 | ord_dataset-3577d334f6eb4dc4bd73564fee3f0dfc | null | 1994-01-01T00:03:00 | true | [CH3:1][NH:2][CH:3]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11]C(=O)C(C)(C)C>Cl>[NH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][CH:3]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[NH:2][CH3:1] | CNC(Cc1ccccc1NC(=O)C(C)(C)C)c1cccnc1 | null | null | Cl | 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 | 8 | A stirred solution of 7.13 g of N-[2-[2-(methylamino)-2-(3-pyridinyl)ethyl]phenyl]-2,2-dimethylpropanamide in 90 ml of 6N hydrochloric acid was refluxed for 5.5 hours and then allowed to stand overnight at room temperature. The solution was decanted over crushed ice, diluted with water (200 ml) and basified with 50% so... | CNC(Cc1ccccc1N)c1cccnc1 | null | 90.1 | null |
1,017,171 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][CH2:20][CH2:21]O)=[CH:14][CH:13]=1)[C:7]([CH3:23])=[CH:6]2.[CH2:24]([N:26](CC)[CH2:27][CH3:28])[CH3:25].CS(Cl)(=O)=O.N1CCCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[CH:14]... | CCN(CC)CC | COc1ccc2c(c1)cc(C)n2-c1ccc(C#CCCO)cc1 | null | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCNC1 | null | null | null | null | null | null | null | null | null | 0 | 2 | To a solution of 4-[4-(5-Methoxy-2-methylindol-1-yl)phenyl]but-3-yn-1-ol (60 mg, 0.19 mmol) in methylene chloride (1 mL) at 0° C. was added triethylamine (54 μL, 0.39 mmol) and methanesulfonylchloride (18 μL, 0.39 mmol). After the solution was stirred at 0° C. for 2 hours, pyrrolidine (163 μL, 1.95 mmol) was added and ... | COc1ccc2c(c1)cc(C)n2-c1ccc(C#CCCN2CCCC2)cc1 | null | 4.1 | null |
1,282,496 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:5]=2[O:4][CH2:3][CH2:2]1.C([Mg]Cl)(C)C.[CH:17]([N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:39])[C:31]1=[O:40])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1.ClCCCl>[C:24]1([CH:17]([C:18]2[CH:23... | Oc1cccc2c1OCCO2 | O=C1C(=O)N(C(c2ccccc2)c2ccccc2)c2ccccc21 | null | CC(C)[Mg]Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCCl | null | null | null | null | null | null | null | null | null | 0 | 0.75 | To a solution of 2,3-dihydro-1,4-benzodioxin-5-ol (3.60 g, 23.7 mmol) in anhydrous tetrahydrofuran (80 mL) at 0° C. was added isopropylmagnesium chloride (11.8 mL, 2 M solution in tetrahydrofuran, 23.7 mmol). The mixture was stirred at 0° C. for 45 min, concentrated in vacuo, and 1,2-dichloroethane (60 mL) was added. T... | O=C1N(C(c2ccccc2)c2ccccc2)c2ccccc2C1(O)c1ccc2c(c1O)OCCO2 | null | 69.3 | null |
1,528,044 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | CO[C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].[NH2:26][CH2:27][CH2:28][O:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+]>CCO>[CH2:16]([N:10]1[C:9](=[O:23])[C:8]2[C:7]([C:24]#[N:25])=[N:6][C:5]([C:3]([... | NCCOCC(=O)O | COC(=O)c1nc(C#N)c2c(=O)n(Cc3ccccc3)ccc2c1O | null | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 150 | null | A mixture of 7-benzyl-1-cyano-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (25 mg, 0.075 mmol), (2-amino-ethoxy)-acetic acid (60 mg, 0.50 mmol), and NaOMe (20 mg, 0.37 mmol) in EtOH (5 mL) was refluxed for 16 h, then heated at 150° C. in a microwave reactor for 2 h. Solvent was evaporat... | N#Cc1nc(C(=O)NCCOCC(=O)O)c(O)c2ccn(Cc3ccccc3)c(=O)c12 | null | 12.6 | null |
1,619,090 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [C:1]([C@@H:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][N:11]3[N:14]=[CH:15][C:16]([C:17]([N:19]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)=[O:18])=[C:10]3[CH:9]=2)[C@@H:5]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[CH:39]=2)[... | COc1ccc(CN(Cc2ccc(OC)cc2)C(=O)c2cnn3ccc(N4C[C@@H](C#N)C[C@@H]4c4cccc(F)c4)cc23)cc1 | [OH-] | null | OO | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 1 | A solution of 5-((2R,4S)-4-cyano-2-(3-fluorophenyl)pyrrolidin-1-yl)-N,N-bis(4-methoxybenzyl)pyrazolo[1,5-a]pyridine-3-carboxamide (I-35) (25 mg, 0.042 mmol) in MeOH (1 mL) was cooled to 0° C. A 1M NaOH solution (0.17 mL, 0.17 mmol) and 30% H2O2 (0.01 mL) were added to the reaction and stirred at 0° C. for 1 hour follow... | COc1ccc(CN(Cc2ccc(OC)cc2)C(=O)c2cnn3ccc(N4C[C@@H](C(N)=O)C[C@@H]4c4cccc(F)c4)cc23)cc1 | null | null | null |
1,688,052 | ord_dataset-c1e70ad912eb438f8d34b1dc681f809a | null | 2016-01-01T00:02:00 | true | [Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[C:14]2[CH3:21].O.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:1][C:12]1[C:11]([O:10][CH3:9])=[CH:20][CH:19]=[C:18]2[C:13]=1[C:14]([CH3:21])=[CH:15][CH:16]=[N:17]2 | O=C1CCC(=O)N1Br | COc1ccc2nccc(C)c2c1 | null | O=S(=O)(O)O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | null | 1 | N-bromosuccinimide (0.57 g, 3.2 mmol) is added at RT to a mixture of 6-methoxy-4-methylquinoline (0.5 g, 2.9 mmol) in conc. sulfuric acid (5 ml). The mixture is stirred for 1 h and poured onto ice-water. The water phase is made basic with an aqueous solution of sodium hydroxide (1 mol/l) and extracted with DCM. The com... | COc1ccc2nccc(C)c2c1Br | null | null | null |
1,589,475 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]2[CH2:17][OH:18])=[CH:4][CH:3]=1.[F:19][C:20]1[CH:21]=[C:22]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:23]=[C:24]([F:27])[C:25]=1O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CCCCCCC>[Cl:1]... | CCOC(=O)CCc1cc(F)c(O)c(F)c1 | OCc1c(C(F)(F)F)ccn1-c1ccc(Cl)cc1 | null | CCCCP(CCCC)CCCC | O=C(N=NC(=O)N1CCCCC1)N1CCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | CCCCCCC | null | null | null | null | null | null | null | null | null | 25 | 3 | A solution of the product prepared in Step D (1.33 g, 4.84 mmol, 1 eq), ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (1.78 g, 7.74 mmol, 1.6 eq), 1,1′-(azodicarbonyl)dipiperidine (2.52 g, 9.68 mmol, 2 eq) and tri-n-butylphosphine (3.08 mL, 12.1 mmol, 2.5 eq) in toluene (85 mL) was heated to 60° C. under N2. After 3... | CCOC(=O)CCc1cc(F)c(OCc2c(C(F)(F)F)ccn2-c2ccc(Cl)cc2)c(F)c1 | null | null | null |
120,323 | ord_dataset-9625b7c45a574cd58946dd2c1803eb6f | null | 1984-01-01T00:07:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O-:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:27]([O:32][CH:33](Br)[CH3:34])(=[O:31])[CH:28]([CH3:30])[CH3:29].[I-].[Na+]>>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3... | CON=C(C(=O)NC1C(=O)N2C(C(=O)[O-])=CCS[C@H]12)c1csc(N)n1 | CC(Br)OC(=O)C(C)C | null | [I-] | [Na+] | 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 | In the same manner as Example 1, sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer) was reacted with 1-bromoethyl isobutyrate in the presence of sodium iodide to give 1-isobutyryloxyethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn-isomer),... | CON=C(C(=O)NC1C(=O)N2C(C(=O)OC(C)OC(=O)C(C)C)=CCS[C@H]12)c1csc(N)n1 | null | null | null |
111,282 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | C([NH:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]=[CH:10]2)(=O)C.[OH-].[Na+]>Cl>[NH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]=[CH:10]2 | CC(=O)Nc1cccc2ccc(=O)[nH]c12 | null | null | Cl | [Na+] | [OH-] | 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 | 0 | null | 8-Acetylaminocarbostyril (21.5 g, 0.106 mol) was suspended in 190 ml of 20% hydrochloric acid and the suspension was stirred while heating under reflux for 1 hour. The reaction mixture was poured into ice water and neutralized with 5 N sodium hydroxide. Crystals which formed were collected by filtration to give 15.47 g... | Nc1cccc2ccc(=O)[nH]c12 | null | 91.1 | null |
261,957 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH3:15][C:16](=[O:21])[CH2:17][C:18](=[O:20])[CH3:19]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:17]([C:16](=[O:21])[CH3:15])[C:18](=[O:20])[CH3:19])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)([O-:3])=[O:2] | CC(=O)CC(C)=O | O=Cc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1 | 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 | null | null | The procedure described in Example 1 was repeated by using 2.53 g 3,5-dinitrobenzaldehyde and 2.43 g of 2,4-pentanedione. Yield 0.8 g, mp 101°-105° C. | CC(=O)C(=Cc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C(C)=O | null | null | null |
701,449 | ord_dataset-bbd7e53f000345838ad4920a07a169ff | null | 2006-01-01T00:03:00 | true | [CH2:1]([O:4][N:5]=[C:6]1[CH2:10][N:9](C(OC(C)(C)C)=O)[C@H:8]([C:18]([OH:20])=O)[CH2:7]1)[CH:2]=[CH2:3].[CH2:21]([N:23]1[C:35]2[CH:34]=[CH:33][C:32]([NH2:36])=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22]>>[CH2:1]([O:4][N:5]=[C:6]1[CH2:10][NH:9][C@H:8]([C:18]([NH:36][C:32]2[CH:33]=[CH:34][C:35]... | CCn1c2ccccc2c2cc(N)ccc21 | C=CCON=C1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1 | 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 | null | null | Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(allyloxy)-imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 80% purity by LC/MS. MS(ESI+): m/z=377.2. | C=CCON=C1CN[C@H](C(=O)Nc2ccc3c(c2)c2ccccc2n3CC)C1 | null | null | null |
221,020 | ord_dataset-42629b4cf1094978a5e5f29f22639ee7 | null | 1991-01-01T00:01:00 | true | [C:1]([C:3](=[C:19]([OH:21])[CH3:20])[C:4]([NH:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)=[O:5])#[N:2].C(C1S[C:27]([C:30]2[CH:35]=CC(F)=C[CH:31]=2)=CC=1)(O)=O>>[C:1]([C:3](=[C:19]([OH:21])[CH3:20])[C:4]([NH:6][C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:30]([CH3:35])([CH3... | CC(O)=C(C#N)C(=O)Nc1ccc(-c2ccc(F)cc2)s1 | O=C(O)c1ccc(-c2ccc(F)cc2)s1 | 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 | null | null | 2-Cyano-N-[5-(4-fluorophenyl)thien-2-yl]-3-hydroxybut-2-enamide, m.p. 232°-234° C. (from 2-carboxy-5-(4-fluorophenyl)thiophene). | CC(O)=C(C#N)C(=O)Nc1ccc(-c2ccc(C(C)(C)C)cc2)s1 | null | null | null |
258,892 | ord_dataset-b17fdf55f5f945a48d47a588fc255573 | null | 1992-01-01T00:12:00 | true | [OH-].[Na+].[CH3:3][C:4]1[C:9]([OH:10])=[C:8]([CH:11]=O)[C:7]([CH2:13][OH:14])=[CH:6][N:5]=1.[ClH:15].Cl.Cl.[O:18]([CH2:20][CH:21]([F:25])[CH2:22][NH:23][CH3:24])[NH2:19]>C(O)C>[ClH:15].[OH:10][C:9]1[C:4]([CH3:3])=[N:5][CH:6]=[C:7]([CH2:13][OH:14])[C:8]=1[CH:11]=[N:19][O:18][CH2:20][CH:21]([F:25])[CH2:22][NH:23][CH3:24... | Cc1ncc(CO)c(C=O)c1O | CNCC(F)CON | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 16 | 4.0 ml of 1N sodium hydroxide solution and 408 mg (2 mmol) of pyridoxal hydrochloride are added to a solution of 390 mg (2.0 mmol) of N-(3-aminoxy-2-fluoropropyl)-methylamine dihydrochloride in 10 ml of ethanol and the mixture is stirred for 16 hours at room temperature. The reaction mixture is then concentrated to dry... | CNCC(F)CON=Cc1c(CO)cnc(C)c1O | null | null | null |
442,828 | ord_dataset-ba7561dae3884c07a8beddd0b9f1222e | null | 1999-01-01T00:10:00 | true | [NH2:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:3]=[CH2:4].[CH:12](OCC)=[O:13]>>[CH:12]([NH:1][C@@H:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:3]=[CH2:4])=[O:13] | CCOC=O | C=C[C@@H](N)Cc1ccccc1 | 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 | null | null | (S)-3-Amino-4-phenyl-1-butene (5.2 g, 35.4 mmol) was dissolved in ethyl formate (100 ml) and the solution was refluxed with heat for 6 hours. After completion of reaction, the solution was concentrated under reduced pressure to give the desired compound as an orange oil. Yield: 6.44 g. | C=C[C@H](Cc1ccccc1)NC=O | null | null | null |
500,685 | ord_dataset-18e9ed24dbd44e98b33bdc22aa7580a8 | null | 2001-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](O)[CH3:13]>>[N+:8]([C:6]1[CH:7]=[C:12]([C:13]2[O:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[N:1]=2)[CH:3]=[CH:4][CH:5]=1)([O-:10])=[O:9] | Nc1cc([N+](=O)[O-])ccc1O | 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 | null | null | 30 | 8 | To 11.5 grams (0.05 mole) of 3-nitrophenylchloroxime are added 150 milliliters of ethanol. To the mixture are added 23.1 grams (0.15 moles) of 2-amino-4-nitrophenol. The mixture is stirred under nitrogen at about 30° C. overnight and filtered to yield 2-(m-nitrophenyl)-5-nitrobenzoxazole. | O=[N+]([O-])c1cccc(-c2nc3cc([N+](=O)[O-])ccc3o2)c1 | null | null | null |
864,204 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | N(C(OCC)=O)=NC(OCC)=O.[OH:13][C@@H:14]1[CH2:19][CH2:18][O:17][C:15]1=[O:16].[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([O:13][C@H:14]2[CH2:19][CH2:18][O:17][C:15]2=[O:16])=[CH:24][CH... | Oc1ccc(C(F)(F)F)cc1 | O=C1OCC[C@H]1O | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0 | 8 | Diethyl azodicarboxylate (2.31 ml, 14.7 mmol) is slowly added to a solution of (R)-(+)-α-hydroxy-γ-butyrolactone (1 g, 9.8 mmol), 4-trifluoromethylphenol (1.58 g, 9.8 mmol) and triphenylphosphine (3.86 g, 14.7 mmol) in anhydrous THF (80 ml) cooled to 0° C. After stirring for 5 minutes at 0° C. and overnight at room tem... | O=C1OCC[C@@H]1Oc1ccc(C(F)(F)F)cc1 | null | null | null |
847,666 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:12]#[N:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:2]2[C:7](=[C:6]([CH:10]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][C:12]#[N:13])[CH:5]=[CH:4][CH:3]=2)[CH:8]=[CH:9]1 | N#CC=C(c1ccccc1)c1ccc2[nH]ccc2c1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 25 | null | To a stirring suspension of 3-(1H-indol-5-yl)-3-phenyl-acrylonitrile VII (2.8 g, 11.5 mmol) in 2-propanol (60 ml) at room temperature, under N2 was added NaBH4 (2.8 g, 74 mmol) portionwise over 90 min period. The mixture was refluxed for 20 hours and additional 2-propanol (25 ml) was added to facilitate the stirring. A... | N#CCC(c1ccccc1)c1cccc2[nH]ccc12 | null | null | null |
1,159,826 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][N:6]1[C:24](=S)[CH2:25][C:26](=O)[CH3:27])=[O:4].[Cl:30][C:31]1[CH:36]=[C:35]([NH:37][NH2:38])[CH:34]=[CH:33][N:32]=1>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S... | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccc(F)cc2C(F)(F)F)CN1C(=S)CC(C)=O | NNc1ccnc(Cl)c1 | 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 | null | null | In analogy to the procedure described in example 192 h, (2S,4R)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-1-(3-oxo-thiobutyryl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with (2-chloro-pyridin-4-yl)-hydrazine (CAS Reg. No. 700811-29-6) to give the title compound as colorless solid. MS (ESI): m/z=547.2... | COC(=O)[C@@H]1C[C@@H](S(=O)(=O)c2ccc(F)cc2C(F)(F)F)CN1c1cc(C)nn1-c1ccnc(Cl)c1 | null | null | null |
290,982 | ord_dataset-5fb693db3950403e9ce1a516570153bf | null | 1994-01-01T00:05:00 | true | [C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](O)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B#B>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | O=C(O)CCCCCCCc1ccccc1 | null | null | B#B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 8-phenyloctanoic acid (19.8 mmol) in sieve dried tetrahydrofuran (5 ml) was reduced with diborane in tetrahydrofuran (30 ml, 29.1 mmol) at 0° C. for 4 hours to give 8-phenyloctanol. To an ice cold solution of the octanol (ca. 19.8 mmol) and carbon tetrabromide (21.98 mmol) in methylene chloride (50 ml) wa... | OCCCCCCCCc1ccccc1 | null | null | null |
1,618,884 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH3:1][C:2]1[S:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][CH:3]=1.Cl[C:17]1[N:22]=[N:21][C:20]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([F:38])[CH:36]=4)[CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1>>[F:38][C:35]1[CH:36]=[C:37]2[C:32]([CH2:31][CH2:30][N:29]2[CH:26]2[CH2:27][CH2:28][N... | Fc1ccc2c(c1)N(C1CCN(c3ccc(Cl)nn3)CC1)CC2 | Cc1ccc(B2OC(C)(C)C(C)(C)O2)s1 | 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 | null | null | The title compound was prepared following the procedure as described in Example 1, Method A, STEP 4, reacting 5-methylthiophene-2-boronic acid pinacol ester and 1-(1-(6-chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline. | Cc1ccc(-c2ccc(N3CCC(N4CCc5ccc(F)cc54)CC3)nn2)s1 | null | null | null |
1,719,874 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:12][C:13]3[O:14][C:15](=[O:29])[C:16]4[C:21]([C:22]=3[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:9]=[C:10](I)[C:3]=12.[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[C:35]([OH:37])[CH:36]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P](... | OB(O)c1cc(O)cc(F)c1 | Nc1ncnc2c1c(I)nn2Cc1oc(=O)c2ccccc2c1-c1ccccc1 | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | 3-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one (intermediate D1, 50 mg, 0.101 mmol), 3-fluoro-5-hydroxyphenylboronic acid (32 mg, 0.201 mmol), Cs2CO3 (69 mg, 0.202 mmol), Pd(PPh3)4 (9.3 mg, 8.0 umol), were reacted in DMF (0.5 mL) at 110° C. under mw irradiation. The resulting c... | Nc1ncnc2c1c(-c1cc(O)cc(F)c1)nn2Cc1oc(=O)c2ccccc2c1-c1ccccc1 | null | 12.4 | null |
1,044,041 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | C([C@H:3]([S:7]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[N:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]3[N:33]([CH3:34])[N:32]=[C:31]([CH3:35])[CH:30]=3)=[O:28])[CH:21]=2)[CH:17]=1)=[O:11])=[O:8])[C:4]([O-:6])=O)C.[NH2:42][CH2:43][CH:44]([O... | NCC(O)CO | CC[C@@H](C(=O)[O-])S(=O)(=NC(=O)c1cncc(C#Cc2cccc(NC(=O)c3cc(C)nn3C)c2)c1)c1ccccc1 | 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 | null | null | In a manner similar to that described in Example 534, (S)-Ethyl[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate and 3-amino-1,2-propanediol were reacted to give the title compound. | Cc1cc(C(=O)Nc2cccc(C#Cc3cncc(C(=O)N=S(=O)(CC(=O)NCC(O)CO)c4ccccc4)c3)c2)n(C)n1 | null | null | null |
121,625 | ord_dataset-fea3ada7aaad45a0b4e7922640986af3 | null | 1984-01-01T00:09:00 | true | [C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][NH:13][C:12]2=[O:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:17]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[H-].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH2:21]([O:20][C:18]([CH:17]([N:13]1[CH2:14][CH... | O=C(Cc1ccccc1)NC1CNC1=O | O=C(OCc1ccccc1)C(Br)c1ccccc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 3-(2-Phenylacetamido)-2-azetidinone (816 mg.) and benzyl 2-bromo-2-phenylacetate (1.22 g.) were dissolved in N,N-dimethylformamide (20 ml.), and to the solution was added sodium hydride (50% oily) (210 mg.) in nitrogen atmosphere under ice-cooling while stirring, and then the reaction mixture was stirred for an hour at... | O=C(Cc1ccccc1)NC1CN(C(C(=O)OCc2ccccc2)c2ccccc2)C1=O | null | null | null |
904,657 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Na].C([CH:4]1[CH2:9][CH2:8][C:7](=[N:10]O)[CH2:6][CH2:5]1)C.O.[CH2:13](O)[CH3:14]>>[CH2:13]([NH:10][CH:7]1[CH2:6][CH2:5][CH2:4][CH2:9][CH2:8]1)[CH3:14] | CCO | CCC1CCC(=NO)CC1 | null | [Na] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | 16 | Sodium (45 g, 1.96 mol) was slowly added to a solution of 4-ethylcyclohexanone oxime (33 g, 0.23 mol) (prepared according to lit. R. O. Hutchins et al. J. Org. Chem. 60 (1995) 7396-7405)) in 99.9% ethanol (500 mL) while keeping the temperature below 65° C. The reaction mixture was heated at reflux temperature for 1½ h ... | CCNC1CCCCC1 | null | null | null |
322,003 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | [Mg].II.Br[CH2:5][CH3:6].[F:7][C:8]([F:18])([F:17])[C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1.Cl>C(Cl)Cl.O1CCCC1>[F:7][C:8]([F:17])([F:18])[C:9]1[CH:10]=[CH:11][C:12]([CH:13]([OH:14])[CH2:5][CH3:6])=[CH:15][CH:16]=1 | O=Cc1ccc(C(F)(F)F)cc1 | CCBr | null | Cl | II | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | 0 | null | Dry tetrahydrofuran (700 mL), magnesium turnings (16.75 g, 0.69 mol, 1.2 eq), and a iodine crystal were placed in a flask and the mixture was stirred intensively at 0° C. Bromoethane (68 g, 46.7 mL, 0.69 mol, 1.1 eq) was added dropwise and the resulting mixture was allowed to stir for 30 min. Then the reaction mixture ... | CCC(O)c1ccc(C(F)(F)F)cc1 | null | null | null |
1,713,703 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OCC)(OCC)(OCC)[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:1]([N:8]1[C:9]2[C:10](=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:16]=[C:17]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | Nc1nc(Cl)ccc1NCc1ccccc1 | CCOC(C)(OCC)OCC | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of N3-benzyl-6-chloropyridine-2,3-diamine (2.56 g, 11.0 mmol, from Step 1), triethyl orthoacetate (15.7 mL, 85.6 mmol, Aldrich) and p-toluenesulfonic acid (0.59 g, 3.4 mmol, Aldrich) in EtOH (55 mL) was heated to reflux for 1.5 hours. The reaction was cooled to room temperature and solvent was evaporated. The... | Cc1nc2nc(Cl)ccc2n1Cc1ccccc1 | null | null | null |
1,039,010 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=O)=[N:5]1)([CH3:3])[CH3:2].[NH2:16][C@H:17]1[CH2:22][N:21]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([CH2:30][CH2:31][OH:32])[CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O>[CH2:23]([N:21]1[C@H:20]([CH2... | CC(C)n1nc(C(=O)O)c2ccccc21 | N[C@@H]1CC[C@H](CCO)N(Cc2ccccc2)C1 | null | CCOP(=O)(C#N)OCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 20 | To a stirred solution of 1-isopropyl-1H-indazole-3-carboxylic acid (235 mg, 1.15 mmol), 2-[cis-5-amino-1-benzylpiperidin-2-yl]ethanol (322 mg, 1.37 mmol, step 8 of Example 1), N,N-diisopropylethylamine (177 mg, 1.37 mmol) in N,N-dimethylformamide (3 mL) was added diethyl cyanophosphonate (223 mg, 1.37 mmol) at room tem... | CC(C)n1nc(C(=O)N[C@H]2CC[C@@H](CCO)N(Cc3ccccc3)C2)c2ccccc21 | null | 57.1 | null |
1,064,778 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [F:1][C:2]([F:21])([F:20])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15]C(C)(C)C)=[O:14])[CH:9]=2)[N:4]=1.FC(F)(F)C(O)=O>ClCCl>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([OH:15])=[O:14])[CH:9]=2)[N:4]=1 | CC(C)(C)OC(=O)c1ccc2nc(C(F)(F)F)ccc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 36 | To a solution of tert-butyl 2-trifluoromethylquinoline-6-carboxylate (2 g, 7 mmol) in dichloromethane (50 mL), cooled to 0° C., was added trifluoroacetic acid (5.18 mL, 67.2 mmol) and the reaction mixture allowed to warm to room temperature and stirred for 36 h. The reaction mixture was concentrated under reduced press... | O=C(O)c1ccc2nc(C(F)(F)F)ccc2c1 | null | 93.6 | null |
156,506 | ord_dataset-36f7bef430f14c2e8db5e3f7c3640d9b | null | 1987-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:11]=[C:12]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23])[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])C>C(O)C>[C:2]1([NH:1][CH:11]=[C:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:14])=[O:15])[S:22... | CCOC=C(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1 | Nc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of aniline (1.0 g) and 2-ethoxy-1,1-bis(phenylsulphonyl)ethene (3.5 g) was heated at 160°-180° C. for 30 minutes, allowing any ethanol evolved to escape. After cooling, the residue was recrystallised by dissolving in a minimum of hot choroform and diluting with between 3 and 4 volumes of ethanol to give 1-phe... | O=S(=O)(C(=CNc1ccccc1)S(=O)(=O)c1ccccc1)c1ccccc1 | null | 80.7 | null |
1,499,042 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [NH2:1]N.[Br:3][C:4]1[CH:16]=[CH:15][C:7]([C:8](/[N:10]=[CH:11]/[N:12](C)C)=O)=[C:6]([F:17])[CH:5]=1>C(O)(=O)C>[Br:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]2[NH:1][N:12]=[CH:11][N:10]=2)=[C:6]([F:17])[CH:5]=1 | CN(C)/C=N/C(=O)c1ccc(Br)cc1F | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 97.5 | 2 | Hydrazine (0.14 mL, 4.4 mmol) was added to a solution of (E)-4-bromo-N-((dimethylamino)methylene)-2-fluorobenzamide (1.105 g, 4.046 mmol) in acetic acid (11 mL). The resulting white suspension was heated to 95-100° C. The resulting solution was stirred at 95-100° C. for 2 hours. The reaction mixture was cooled to ambie... | Fc1cc(Br)ccc1-c1ncn[nH]1 | null | 114 | null |
502,605 | ord_dataset-d673d02cdac14dba9ff59f12845a4f37 | null | 2001-01-01T00:05:00 | true | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][C:12]2[NH:13][C:14](=[O:25])[C:15]3[N:20]([CH3:21])[N:19]=[C:18]([CH2:22][CH2:23][CH3:24])[C:16]=3[N:17]=2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH3:21][N:20]1[C:15]2[C:14](=[O:25])[NH:13][C:12]([CH2:11][C:10]3[CH:26]=[CH:27][C:7]([NH:6][S:2]([CH3:1])(=[... | CCCc1nn(C)c2c(=O)[nH]c(Cc3ccc(N)cc3)nc12 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 2 | Methanesulfonyl chloride (43 μl, 0.00055 mol) was added to a solution of 5-(4-aminobenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-7-one (150 mg, 0.0005 mol) in pyridine (5 ml), and the reaction stirred at room temperature, under a nitrogen atmosphere for 2 hours. | CCCc1nn(C)c2c(=O)[nH]c(Cc3ccc(NS(C)(=O)=O)cc3)nc12 | null | null | null |
44,055 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | C([O:3][C:4](=O)[NH:5][N:6]=[CH:7][C:8]1[N:9]=[C:10]([CH2:13][CH2:14][CH3:15])[NH:11][CH:12]=1)C.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH2:13]([C:10]1[N:9]2[C:4](=[O:3])[NH:5][N:6]=[CH:7][C:8]2=[CH:12][N:11]=1)[CH2:14][CH3:15] | CCCc1nc(C=NNC(=O)OCC)c[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccc(Oc2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | An 8.75 gm. portion of 3-(2-n-propyl-4-imidazolylmethylene)carbazic acid ethyl ester in 50 ml. of diphenyl ether is reacted as described in Example 70 giving the desired product, m.p. 159°-162.5° C. | CCCc1ncc2cn[nH]c(=O)n12 | null | null | null |
1,150,335 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH3:1][NH:2][C:3]([C:5]1[CH:9]=[C:8]([Cl:10])[S:7][C:6]=1[Cl:11])=[O:4].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[CH3:1][NH:2][C:3]([C:5]1[C:9]([N+:12]([O-:14])=[O:13])=[C:8]([Cl:10])[S:7][C:6]=1[Cl:11])=[O:4] | O=[N+]([O-])O | CNC(=O)c1cc(Cl)sc1Cl | null | O=S(=O)(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 | 0 | 1 | An ice-cold mixture of 2,5-dichloro-thiophene-3-carboxylic acid methylamide (475 mg) in H2SO4 (20 mL, 95-98%) was treated with fuming HNO3 (25 mL). The mixture was stirred for 1 hour and slowly poured onto ice, extracted with ethyl acetate three times, and dried over sodium sulfate. Filtration and concentration provide... | CNC(=O)c1c(Cl)sc(Cl)c1[N+](=O)[O-] | null | null | null |
78,158 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | C([NH:4][C:5]1[S:6][C:7]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[N:8][N:9]=1)(=O)C.Cl>>[NH2:4][C:5]1[S:6][C:7]([S:10]([N:13]([CH3:15])[CH3:14])(=[O:11])=[O:12])=[N:8][N:9]=1 | CC(=O)Nc1nnc(S(=O)(=O)N(C)C)s1 | null | null | Cl | 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 | 25 | null | 2-Acetamido-5-(N,N-dimethylaminosulfonyl)-1,3,4-thiadiazole (250 grams) and concentrated hydrochloric acid (1 L) were charged into a glass reaction vessel fitted with a mechanical stirrer, reflux condenser and thermometer. This mixture was refluxed for a period of about 2 hours. It was then cooled to room temperature, ... | CN(C)S(=O)(=O)c1nnc(N)s1 | null | null | null |
740,170 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([N:8]=[C:9]=[S:10])[CH:7]=1.Cl.CN.[CH2:15]([N:17](CC)CC)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([NH:8][C:9]([NH:17][CH3:15])=[S:10])[CH:7]=1 | Cc1ccc(Cl)cc1N=C=S | CCN(CC)CC | null | CN | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | null | 5-Chloro-2-methylphenyl isothiocyanate (36.6 g; 0.2 mol) was added to the solution of methylamine hydrochloride (26.8 g; 0.4 mol) in chloroform (300 mL). Triethylamine (65 mL; 0.47 mol) was added dropwise while stirring at ambient temperature. The mixture was stirred for 18 hours. The solvent was evaporated. The residu... | CNC(=S)Nc1cc(Cl)ccc1C | null | 96.9 | null |
1,558,748 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:29][C:30]2[CH:35]=[CH:34][C:33](=[O:36])[N:32]([CH3:37])[CH:31]=2)[C:9]2[C:10]([C:24]([O:26]CC)=[O:25])=[N:11][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:13]=2[CH3:14])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([... | CCOC(=O)c1nn(Cc2ccc(OC)cc2)c(C)c1C(Nc1ccc(=O)n(C)c1)c1ccc(Cl)cc1 | null | null | [Li]O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 3 | In a 25-mL flask was introduced ethyl 4-((4-chlorophenyl)(1-methyl-6-oxo-1,6-dihydropyridin-3-ylamino)methyl)-1-(4-methoxybenzyl)-5-methyl-1H-pyrazole-3-carboxylate (Step 1.4) (140 mg, 0.269 mmol) and LiOH.H2O (33.8 mg, 0.806 mmol) in dioxane (2.5 mL) and H2O (1.0 mL). The reaction mixture was stirred for 3 hr at rt, q... | COc1ccc(Cn2nc(C(=O)O)c(C(Nc3ccc(=O)n(C)c3)c3ccc(Cl)cc3)c2C)cc1 | null | 96.7 | null |
606,899 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [CH2:1]([OH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14]Cl.O>CN(C=O)C>[CH3:11][N:12]([CH3:16])[CH2:13][CH2:14][O:7][CH2:1][C:2]1[O:6][CH:5]=[CH:4][CH:3]=1 | CN(C)CCCl | OCc1ccco1 | null | Cl | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0.25 | Furfuryl alcohol (10.0 g, 102 mmol) was dissolved in DMF (200 ml) and sodium hydride (60% dispersion in oil, 9.00 g, 225 mmol) was added under ice-cooling. The mixture was stirred for 15 min at the same temperature. Then, 2-dimethylaminoethyl chloride hydrochloride (15.4 g, 107 mmol) was added under ice-cooling and the... | CN(C)CCOCc1ccco1 | null | 24.3 | null |
901,479 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([CH:22]=[CH:23][C:24]([OH:26])=[O:25])([CH2:18][CH2:19]3)[CH2:16][O:15]4)[NH:6][C:5]=2[C:4](=[O:27])[N:3]1[CH2:28][CH2:29][CH3:30]>CO.[Pd]>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C... | CCCn1c(=O)c2[nH]c(C34CCC(C=CC(=O)O)(CC3)CO4)nc2n(CCC)c1=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 0.5 | 3-[1-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-2-oxa-bicyclo[2.2.2]oct-4-yl]-acrylic acid was dissolved in 50 ml of MeOH. 10% Pd on C (10 mg) was added and the reaction mixture was hydrogenated at RT under 55 psi of H2 for 30 min. The reaction mixture was filtered through a pad of Celite and the filtrat... | CCCn1c(=O)c2[nH]c(C34CCC(CCC(=O)O)(CC3)CO4)nc2n(CCC)c1=O | null | null | null |
179,625 | ord_dataset-ed5a3d1f8dc744759e7fa1c320a44e59 | null | 1988-01-01T00:11:00 | true | [CH3:1][C:2]1[N:10]([CH3:11])[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[N:3]=1.[Se](=O)=[O:13]>O1CCOCC1>[CH3:11][N:10]1[C:5]2[CH:6]=[N:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:1]=[O:13] | O=[Se]=O | Cc1nc2ccncc2n1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | Employing the procedure of Example 10B and starting with 774 mg of 2,3-dimethyl-3H-imidazo[4,5-c]pyridine (Preparation J2) and 584 mg of selenium dioxide in 30 ml of dioxane, there was obtained 442 mg of the desired product. | Cn1c(C=O)nc2ccncc21 | null | 52.2 | null |
236,169 | ord_dataset-1acb071a357f438ea5993287375971cf | null | 1991-01-01T00:10:00 | true | [Cl:1][C:2]1[C:25]([F:26])=[C:24]([Cl:27])[CH:23]=[C:22](F)[C:3]=1[C:4]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:25]([F:26])=[C:24]([Cl:27])[CH:23]=[C:22]2[C:3]=1[C:4](=[O:5])[C:6]([C:7]([O... | CCOC(=O)C(=CNc1ccc(F)cc1F)C(=O)c1c(F)cc(Cl)c(F)c1Cl | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | 0 | null | 43.6 g of ethyl 2-(2,4-dichloro-3,6-difluorobenzoyl)-3-(2,4-difluorophenylamino)-acrylate are heated in 260 ml of dimethylformamide at 150° C. with 15.2 g of potassium carbonate for 2.5 hours. The mixture is poured into 1 liter of ice-water and the precipitate is filtered off with suction, washed with water and dried. ... | CCOC(=O)c1cn(-c2ccc(F)cc2F)c2cc(Cl)c(F)c(Cl)c2c1=O | null | 92.8 | null |
1,619,277 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | C[O:2][C:3](=O)[C:4]([C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[N+:19]([O-])=O)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5]>C(O)(=O)C.[Fe]>[Br:18][C:16]1[CH:17]=[C:12]2[C:13](=[CH:14][CH:15]=1)[NH:19][C:3](=[O:2])[C:4]2([CH3:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1 | COC(=O)C(C)(c1ccccc1)c1cc(Br)ccc1[N+](=O)[O-] | null | null | [Fe] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 70 | 3 | A mixture of 2-(5-Bromo-2-nitro-phenyl)-2-phenyl-propionic acid methyl ester (5.9 g, 16.25 mmol) and iron powder (3.64 g, 65 mmol) in acetic acid (100 mL) is heated to 70° C. and stirred for 3 hours. The acetic acid is removed in vacuo. The residue is diluted with satu. aq. NH4Cl solution and extracted with ethyl aceta... | CC1(c2ccccc2)C(=O)Nc2ccc(Br)cc21 | null | null | null |
383,857 | ord_dataset-f367d8d2baac490b9204609a79420961 | null | 1997-01-01T00:11:00 | true | [CH2:1](/[C:3](=[CH:8]\[CH3:9])/[CH:4]=[CH:5]/[CH2:6][OH:7])[CH3:2].[O-:10][C:11]#[N:12].[Na+].FC(F)(F)C(O)=O>C1C=CC=CC=1>[C:11](=[O:10])([O:7][CH2:6][CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH3:9])[NH2:12] | C/C=C(/C=C/CO)CC | N#C[O-] | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | 2 | To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (3.0 g), sodium cyanate (3.1 g), and benzene (15 ml) at room temperature was added dropwise trifluoroacetic acid (5.42 g) during 1 hour. After being stirred for 2 hours at the same temperature, the reaction mixture was partitioned between water and ethyl acetate. The orga... | CC=C(C=CCOC(N)=O)CC | null | 49.7 | null |
1,219,392 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([NH:13][CH:14]([CH3:16])[CH3:15])[N:7]=1)=O)C.[NH3:17]>CO>[CH:14]([NH:13][C:8]1[N:7]=[C:6]([C:4]([NH2:17])=[O:3])[CH:11]=[C:10]([CH3:12])[N:9]=1)([CH3:16])[CH3:15] | N | CCOC(=O)c1cc(C)nc(NC(C)C)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid ethyl ester (1.46 g, 6.54 mmol) in 3M NH3 in MeOH (50 mL) is stirred at 60° C. for 1 day. Volatiles are evaporated to give the crude 2-isopropylamino-6-methyl-pyrimidine-4-carboxylic acid amide as a pale yellow solid (1.24 g); LC-MS: tR=0.59; [M+H]+=1... | Cc1cc(C(N)=O)nc(NC(C)C)n1 | null | null | null |
1,618,651 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH2:21][CH3:22])=[N:19][N:20]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.Cl>CO>[CH2:21]([C:18]1[O:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=2)=[N:20][N:19]=1)[CH3:22] | CCc1nnc(-c2ccc(CO[Si](C)(C)C(C)(C)C)cc2)o1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To an ice-cold solution of 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)-5-ethyl-1,3,4-oxadiazole (3.0 g, 9.4 mmol) in MeOH (30 mL) was added 1 M HCl (20 mL, 20 mmol) dropwise. The reaction was stirred over ice for 1 hr then concentrated. The residue was quenched with saturated aqueous NaHCO3 and extracted with Et... | CCc1nnc(-c2ccc(CO)cc2)o1 | null | 100 | null |
1,001,822 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | C[O:2][C:3](=[O:32])[CH2:4][CH2:5][NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25](Br)=[C:24]([CH3:30])[CH:23]=2)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=1.[CH:33]([C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1)([CH3:35])[CH3:34]>>[F:18][C:17](... | COC(=O)CCNC(=O)c1ccc(C(CCC(F)(F)F)Oc2cc(C)c(Br)c(C)c2)cc1 | CC(C)c1ccc(B(O)O)cc1 | 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 | null | null | The title compounds are prepared in a manner substantially similar to Example 128 starting from enantiomers of 3-{4-[1-(4-bromo-3,5-dimethyl-phenoxy)-4,4,4-trifluoro-butyl]-benzoylamino}-propionic acid methyl ester and 4-isopropyl phenyl boronic acid. Isomer 1 MS: 540.2 [M−H]−, Isomer 2 MS: 540.2 [M−H]−. | Cc1cc(OC(CCC(F)(F)F)c2ccc(C(=O)NCCC(=O)O)cc2)cc(C)c1-c1ccc(C(C)C)cc1 | null | null | null |
293,359 | ord_dataset-b90b48a6c23149a1aa2d91b92b1a31e4 | null | 1994-01-01T00:07:00 | true | [Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:7](Cl)=[O:8]>C1(C)C=CC=CC=1>[CH3:5][CH:6]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:7]1=[O:8] | Cc1ccccc1CC(C)C(=O)Cl | null | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 80 | 4 | 36 g (270 mmol) of AlCl3 were added to 17.7 g (90 mmol) of acid chloride f4 in 50 ml of toluene in the course of 20 minutes, and the mixture was stirred at 80° C. for 4 hours. It was poured onto ice/HCl, extracted with toluene, washed with H2O, NaHCO3 solution and NaCl solution, dried and distilled (109° C./1 mmHg) or ... | Cc1cccc2c1CC(C)C2=O | null | null | null |
939,969 | ord_dataset-90b0aa1f83334a02919b2be3a1c04542 | null | 2010-01-01T00:02:00 | true | [Cl:1][C:2]1[N:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.[C:23]1(=[O:28])[CH2:27][CH2:26][CH:25]=[CH:24]1>CO.O>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:24]2[C:23](=[O:28])[CH2:27][CH2:26][CH:25]=2)=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])... | O=C1C=CCC1 | COc1ccc(-c2cnc(Cl)c(C=O)c2)cc1 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | The clear solution of 2-Chloro-5-(4-methoxyphenyl)-nicotinaldehyde (10 mmol, 2.45 g) and imidazole (10 mmol) in 50 ml. of MeOH was slowly charged with 50 ml. of deionized water. To a stirred homogeneous reaction mixture was added 2-cyclopenten-1-one (10.2 mmol. 0.88 g) at room temperature and reaction progress was moni... | COc1ccc(-c2cnc(Cl)c(C(O)C3=CCCC3=O)c2)cc1 | null | 90 | null |
657,663 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)(O)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[O:21]([C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:16][CH:17]=1)[C:22]1[CH:23]=[CH:2... | CC(C)(C)OC(=O)N1CCC(O)(c2ccc(Oc3ccccc3)cc2)CC1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | To a 3 ml of methylene chloride solution of 772 mg of N-tert-butoxycarbonyl-4-(4-phenoxyphenyl)-4-piperidinol synthesized in Step A, a 3 ml of trifluoroacetic acid was dropwise added under ice cooling. The resultant mixture was stirred at room temperature for 2-hours, then adjusted by 10% aqueous sodium hydroxide solut... | C1=C(c2ccc(Oc3ccccc3)cc2)CCNC1 | null | 47 | null |
1,010,185 | ord_dataset-7448b89163bf426c9d9777809ce24cec | null | 2010-01-01T00:11:00 | true | C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([CH3:17])[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O>[CH3:17][C:7]1[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1 | COC(=O)c1ccc(-c2ccccc2)c(C)c1 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | A solution of 2-methyl-biphenyl-4-carboxylic acid methyl ester (0.10 g, 0.44 mmol) in CH3OH (5 mL) and H2O (0.5 mL) is reacted with NaOH (88 mg, 2.2 mmol) at reflux for 2 h. Organic solvent is removed in vacuo, the residue is diluted with H2O, and extracted with Et2O. The aqueous layer is acidified with 5 M HCl, extrac... | Cc1cc(C(=O)O)ccc1-c1ccccc1 | null | 77.1 | null |
847,100 | ord_dataset-e2b35e721c2741999b0005d12691f9fe | null | 2008-01-01T00:10:00 | true | C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:23]=[CH:22][C:21]2[N:20]3[C:16](=[N:17][N:18]=[C:19]3[CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[CH2:26][CH2:25]3)[CH2:15][NH:14][CH2:13][CH2:12][C:11]=2[CH:10]=1.C(N(CC)CC)C>ClCCl>[Cl:8][C:9]1[CH:23]=[CH:22][C:21]2[N:20]3[C:16](=[N:17][N:1... | CC(=O)OC(C)=O | Clc1ccc2c(c1)CCNCc1nnc(C3CCN(c4ccccn4)CC3)n1-2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 2 | Acetic anhydride (35 □l, 0.37 mmol) was added to a solution of the amine of example 22 (120 mg, 0.30 mmol) and triethylamine in dichloromethane (5 ml) and stirred at room temperature for 2 hours. The dichloromethane was evaporated off under reduced pressure and the residue was purified by chromatography on silica gel u... | CC(=O)N1CCc2cc(Cl)ccc2-n2c(nnc2C2CCN(c3ccccn3)CC2)C1 | null | 91.5 | null |
138,396 | ord_dataset-3fa0a6b7d51b4fc6a5380aa0d03ac884 | null | 1985-01-01T00:12:00 | true | Br[CH:2]([CH:13]([CH3:16])[CH2:14]Br)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH2:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[CH2:6]([O:5][C:3]([C@H:2]1[C@@H:13]([CH3:16])[CH2:14][N:17]1[CH:18]([C:19]1[CH:24]=[CH:23][CH:22... | NC(c1ccccc1)c1ccccc1 | CC(CBr)C(Br)C(=O)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A stirred mixture of 23.94 g of 3D, 37.6 g of aminodiphenylmethane and 170 ml of acetonitrile was refluxed for 40 hours. The mixture was cooled, filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in the minimum amount of methylene chloride, the solution was filtered ... | C[C@H]1CN(C(c2ccccc2)c2ccccc2)[C@H]1C(=O)OCc1ccccc1 | null | null | null |
1,576,022 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [Si]([O:8][CH2:9][C:10]1[O:15][C:14](=O)[C:13]2[S:17][C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[C:12]=2[C:11]=1[C:24]1[C:25]([CH3:34])=[C:26]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][CH2:28][CH2:27]2)(C(C)(C)C)(C)C.[CH3:35][NH2:36]>CCO>[OH:8][CH2:9][C:10]1[N:36]([CH3:35])[C:14](=[O:15])[C:13]2[S:17][C:18]3[CH2:23][... | Cc1c(-c2c(CO[Si](C)(C)C(C)(C)C)oc(=O)c3sc4c(c23)CCCC4)ccc2c1CCCO2 | CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 65 | 3 | 3-(((tert-butyldimethylsilyl)oxy)methyl)-4-(5-methylchroman-6-yl)-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-c]pyran-1-one (100 mg, 0.2 mmol) was dissolved in 4N MeNH2 (g)/EtOH (20 mL) and stirred at 65° C. for 3 hrs. After cooling to room temperature, the mixture was concentrated, and 4N HCl/ethyl acetate (20 ml) was ... | Cc1c(-c2c(CO)n(C)c(=O)c3sc4c(c23)CCCC4)ccc2c1CCCO2 | null | 75 | null |
837,869 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13]Br)=[CH:6][C:5]=1[NH:15][C:16](=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([F:26])([F:25])[F:24].[C:29]([C:33]1[CH:41]=[CH:40][C:36]([CH:37]=[N:38][OH:39])=[CH:35][CH:34]=1)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([C:33]1[CH:41]=[CH:... | CC(C)(C)c1ccc(C=NO)cc1 | COC(=O)c1ccc(OCCCBr)cc1NC(=O)c1ccccc1C(F)(F)F | 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 | null | null | The title compound (0.117 g, 64%) was prepared as a white solid from 4-(3-bromo-propoxy)-2-(2-trifluoromethyl-benzoylamino)-benzoic acid methyl ester and 4-tert-butyl-benzaldehyde oxime using a procedure similar to step 1 of example 6. mp=121.1-122.0° C.; mass spectrum API-ES, (M−H) m/z 541. 1H NMR (400 MHz, DMSO-d6); ... | CC(C)(C)c1ccc(/C=N/OCCCOc2ccc(C(=O)O)c(NC(=O)c3ccccc3C(F)(F)F)c2)cc1 | null | 64 | null |
764,318 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:3]=1.P(Br)(Br)[Br:16].N>O>[Br:16][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:3]=1 | Clc1ccc(-c2cncc(Cl)n2)cc1 | BrP(Br)Br | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 25 | null | To a flask containing 2-chloro-6-(4-chlorophenyl)pyrazine (2.35 g, 10.4 mmol), was added phosphorus tribromide (17 mL) and the mixture heated at reflux for 6 h under nitrogen. The reaction mixture was cooled to room temperature prior to pouring carefully into iced water (600 mL) the resulting mixture was adjusted to pH... | Clc1ccc(-c2cncc(Br)n2)cc1 | null | null | null |
763,997 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[CH:24]=[C:25]([NH:30][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:26]=[CH:27][C:28]=2[CH3:29])[CH2:19][CH2:18]1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([CH3:12])[C:9]... | C[C@@H](C(=O)O)c1ccc(F)cc1 | Cc1ccc(NC(=O)C(C)C)cc1C1CCN(CCCN)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Example 169 was prepared from (2R)-2-(4-fluorophenyl)propanoic acid and N-{3-[1-(3-aminopropyl)-4-piperidinyl]-4-methylphenyl}-2-methylpropanamide according to the procedures described in Scheme 12; [α]D=−9.1° (C=1.65, MeOH): 1H NMR (400 MHz, CDCl3) δ 7.51 (d, 1 H, J=2.0 Hz), 7.37–7.28 (m, 2 H), 7.23–7.14 (m, 2 H), 7.0... | Cc1ccc(NC(=O)C(C)C)cc1C1CCN(CCCNC(=O)[C@H](C)c2ccc(F)cc2)CC1 | null | null | null |
711,914 | ord_dataset-c8a367b56b4f406b878f51867b157d19 | null | 2006-01-01T00:06:00 | true | [NH2:1][C:2]1[C:3]([SH:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:11][CH2:12][C:13](OCC)(OCC)OCC>C(O)C>[Cl:11][CH2:12][C:13]1[S:10][C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=2 | CCOC(CCl)(OCC)OCC | COc1ccc(N)c(S)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 90 | null | 3-Amino-6-methoxy-2-pyridinethiol (0.8 g, Maybridge Co.) and 2-chloro-1,1,1-triethoxyethane (1.26 g) were combined in ethanol (5 mL) and heated at 90° C. in a sealed tube for 2 hours. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue w... | COc1ccc2nc(CCl)sc2n1 | null | null | null |
196,092 | ord_dataset-a58d1baeeea441fb9918c10f18f2cdb9 | null | 1989-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[C:25]1([CH2:31][CH2:32][CH2:33][CH2:34]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOCC>COCCOC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:11][C:12]1[C:... | CCOC(=O)C(Cc1cccc2ccccc12)C(=O)OCC | BrCCCCc1ccccc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCOC | CCOCC | null | null | null | null | null | null | null | null | null | null | null | To a solution of 2.62 g of 2-(1-naphthylmethyl)malonic acid diethyl ester in 40 ml of dry 1,2-dimethoxyethane was added 0.46 g of a 50% sodium hydride (suspension in oil) while ice-cooling, and then 2.05 g of 4-phenylbutyl bromide was added dropwise to the mixture. The mixture was heated under reflux for 19 hours. Afte... | CCOC(=O)C(CCCCc1ccccc1)(Cc1cccc2ccccc12)C(=O)OCC | null | 73.4 | null |
1,133,989 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[NH:38]1[CH:42]=[CH:41][N:40]=[CH:39]1>>[F:1][C:2]1[CH:3]=[C:4](... | c1c[nH]cn1 | CS(=O)(=O)c1nccc(Oc2ccc(NC(=O)c3cc(F)cc(N4CCCCC4)c3)c3ccccc23)n1 | 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 | null | null | Compound is prepared from 3-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide and imidazole according to conditions described in general procedure C. Mp: 175-176° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.58-1.60 (m, 6 H), 3.28-3.31 (m, 4 H), 6.96 (d, J=12.4, 1 H), 7.03-7.04 (m, 1 H)... | O=C(Nc1ccc(Oc2ccnc(-n3ccnc3)n2)c2ccccc12)c1cc(F)cc(N2CCCCC2)c1 | null | null | null |
207,756 | ord_dataset-ac1c7aa04d6c4e588e723e3e05721681 | null | 1990-01-01T00:05:00 | true | [NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[N:6]=1.[CH3:28][N:29]=[C:30]=[O:31].[OH-].[Na+]>O1CCCC1>[CH3:28][NH:29][C:30](=[O:31])[NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:... | CN=C=O | Nc1nc(CN2CCC(OC(c3ccccc3)c3ccccc3)CC2)cs1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 3 | To a stirred solution of 2-amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (1.0 g) in dry tetrahydrofuran (10 ml) was added dropwise methyl isocyanate (0.34 ml) at ambient temperature. After the addition had been completed, the reaction mixture was stirred for 3 hours. 1N Sodium hydroxide solution (3 ml) was adde... | CNC(=O)Nc1nc(CN2CCC(OC(c3ccccc3)c3ccccc3)CC2)cs1 | null | null | null |
1,523,632 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:20][C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[Cl:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5] | N#Cc1ccc(F)cc1Cl | COc1ccc(O)c(Cl)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 120 | 2 | A solution of 3.0 g (19.28 mmol) of 2-chloro-4-fluorobenzonitrile and 3.06 g (19.28 mmol) of 2-chloro-4-methoxyphenol in 77 mL DMSO was combined with 5.32 g (38.57 mmol) of potassium carbonate and stirred for 2 h at 120° C. Then the mixture was evaporated to dryness in vacuo, the residue was taken up in dichloromethane... | COc1ccc(Oc2ccc(C#N)c(Cl)c2)c(Cl)c1 | null | null | null |
749,871 | ord_dataset-844a22e1fcab44a5b59c5e2922b2855a | null | 2007-01-01T00:01:00 | true | [CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22](O)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=1[N:34]1[C@H:38]([CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43... | CC(C)(C)[Si](C)(C)OC[C@@H]1CCC(=O)N1c1cc(F)ccc1CN | CC1(C)OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=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 | null | null | null | null | The title compound can be prepared from intermediate 27, 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido-[2,1-c][1,4]oxazine-2-carboxylic acid and (S)-1-(2-(aminomethyl)-5-fluorophenyl)-5-((tert-butyldimethylsilyloxy)methyl)pyrrolidin-2-one, derived from reduction of intermediate 122, (R)-2-(2-((tert-butyld... | CC1(C)OCCn2c1nc(C(=O)NCc1ccc(F)cc1N1C(=O)CC[C@@H]1CO[Si](C)(C)C(C)(C)C)c(OCc1ccccc1)c2=O | null | null | null |
698,613 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | [C:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)(=[O:3])[NH2:2].[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1.C(O)C>CN(C)C=O>[Si:9]([O:8][CH:6]1[CH2:7][N:4]([C:1](=[O:3])[NH2:2])[CH2:5]1)([C:22]([CH3:25])([CH3:24])[CH3:23... | NC(=O)N1CC(O)C1 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1 | null | c1c[nH]cn1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCO | null | null | null | null | null | null | null | null | null | null | 0.17 | To a solution of 1-carbamoyl-3-hydroxyazetidine (obtained as described in Reference Example 21(1)) in dimethylformamide (100 ml) were added t-butyldiphenylsilyl chloride (18.0 ml, 66.9 mmol) and imidazole (4.55 g, 66.9 mmol) in an ice bath. After stirring the mixture in an ice bath for 10 minutes, the resulting mixture... | CC(C)(C)[Si](OC1CN(C(N)=O)C1)(c1ccccc1)c1ccccc1 | null | 18 | null |
20,293 | ord_dataset-2a1960001e7d4e89987253631df1362a | null | 1977-01-01T00:02:00 | true | [NH:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][N:4]=1)[NH2:2].[CH:17](=O)[CH3:18].S(=O)(=O)(O)O>>[CH:17](=[N:2][NH:1][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[CH2:6][CH2:5][N:4]=1)[CH3:18] | COc1cc2c(cc1OC)C(NN)=NCC2 | CC=O | null | O=S(=O)(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 | null | null | In a manner similar to that of Step C of Example 1, condensation of 1-hydrazino-6,7-dimethoxy-3,4-dihydroisoquinoline (7.2 g.) with acetaldehyde (4.3 g.) and treatment of the resulting product with sulfuric acid afforded 1-(2-ethylidenehydrazino)-6,7-dimethoxy-3,4-dihydroisoquinoline (I: X=CH3, X' =Y=Y' =H, Z=Z' =CH3O)... | CC=NNC1=NCCc2cc(OC)c(OC)cc21 | null | null | null |
1,457,495 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([NH:12][NH2:13])=[O:11])=[CH:5][C:4]=1[O:16][CH3:17].[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[S:27])=[CH:21][CH:20]=1.CCN(CC)CC>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:15])([CH3:14])[C:10]([NH:12][NH:13][C:26](=[S:27])[NH:25][C:22]2[CH... | COc1cc(C(C)(C)C(=O)NN)ccc1Cl | Fc1ccc(N=C=S)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1.5 | To a solution of 2-(4-chloro-3-methoxyphenyl)-2-methylpropanehydrazide hydrochloride (6.88 g, 0.02 mol) and 4-fluorophenylisothiocyanate (3.96 g, 0.03 mol, 1.05 eq.) in DCM (500 mL) at 0° C. was added Et3N (7 mL, 1.29 mol, 2.0 eq.) and the resulting solution was stirred for 1.5 h at room temperature. The reaction mixtu... | COc1cc(C(C)(C)C(=O)NNC(=S)Nc2ccc(F)cc2)ccc1Cl | null | null | null |
1,033,882 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9](OS(C)(=O)=O)[CH2:8][C@H:7]1[C:16]([N:18]1[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19]1)=[O:17])=[O:5])[CH3:2].[Cl:25][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[SH:33]>>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([S:33][C:27]2[CH:28]=[CH:29][C:30]([F:32])=[CH:31][... | CCOC(=O)[C@@H]1C[C@H](OS(C)(=O)=O)C[C@H]1C(=O)N1CCC(F)(F)C1 | Fc1ccc(S)c(Cl)c1 | 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 | null | null | The title compound was prepared in analogy to example 68/69 step 8 using (1R,2R,4R)-2-(3,3-Difluoro-pyrrolidine-1-carbonyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester (example 186 step 3) and 2-chloro-4-fluorothiophenol. Light yellow oil (88%). MS (EI): 436.1 (M+H)+. | CCOC(=O)[C@@H]1C[C@@H](Sc2ccc(F)cc2Cl)C[C@H]1C(=O)N1CCC(F)(F)C1 | null | null | null |
783,447 | ord_dataset-4ad5db8537994579bef51f16dd8bf0bd | null | 2007-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:18])=[CH:5][CH:4]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>C1COCC1>[C:34]([O:33][C:31](=[O:32])[CH2:30][CH:10]1[CH2:11][C:12]2[C:17](=[CH:16][CH:15... | COc1ccc(CN2C(=O)CCc3ccccc32)cc1 | CC(C)(C)OC(=O)CBr | null | CC(C)[N-]C(C)C | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 0.17 | The 1-(4-methoxy-benzyl)-3,4-dihydro-1H-quinolin-2-one (7.86 mmol) obtained in the previous step is dissolved in 10 mL of anhydrous THF. A solution of freshly prepared LDA (9.43 mmol) in 3.5 mL of anhydrous THF is added dropwise at −78° C. The reaction mixture is stirred at −78° C. for 10 minutes, warmed up to 0° C. fo... | COc1ccc(CN2C(=O)C(CC(=O)OC(C)(C)C)Cc3ccccc32)cc1 | null | 53 | null |
822,653 | ord_dataset-ec58fad8331a42c5a67ad75aac6713b4 | null | 2008-01-01T00:05:00 | true | Cl[C:2]1[CH:19]=[C:6]2[C:7]3[C:12]([CH2:13][CH2:14][N:5]2[C:4](=[O:20])[N:3]=1)=[CH:11][C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=3.[CH3:21][C:22]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:23]=1[NH2:24]>CC(O)C>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:17][CH3:18])[C:6]1=[CH:19][C:2](=[... | Cc1cc(C)c(N)c(C)c1 | COc1cc2c(cc1OC)-c1cc(Cl)nc(=O)n1CC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | null | null | null | null | null | null | null | null | null | null | 25 | null | 2-Chloro-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one, prepared according to Preparation 1, (38.5 g, 0.13 mol) and 2,4,6-trimethylaniline (52.7 g, 0.39 mol) in propan-2-ol (31) was stirred and heated at reflux, under nitrogen, for 24 h. After cooling to room temperature, the solution was evaporated in... | COc1cc2c(cc1OC)-c1cc(=Nc3c(C)cc(C)cc3C)[nH]c(=O)n1CC2 | null | null | null |
681,113 | ord_dataset-3947f3e1be17462c8f7c7e6ea6e57d0a | null | 2005-01-01T00:08:00 | true | [Mg].[CH2:2]([C:4]1[C:12]2[N:11]3[C@H:13]([CH3:18])[CH2:14][NH:15][C:16](=[O:17])[C:10]3=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:3].[H][H].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO>[CH2:2]([C:4]1[C:12]2[N:11]3[C@H:13]([CH3:18])[CH2:14][NH:15][C:16](=[O:17])[C@@H:10]3[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:3] | [H][H] | CCc1cccc2cc3n(c12)[C@H](C)CNC3=O | null | O=P([O-])([O-])[O-] | [K+] | [Mg] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 0 | 2 | Magnesium turnings (87 mg, 3.6 mmol) were added to a solution of (R)-6-Ethyl-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (82 mg, 0.36 mmol) in methanol (4 mL). After hydrogen gas started to evolve, the reaction mixture was kept at 10-20° C. and stirred for 2 h to dissolve the magnesium completely. Then the react... | CCc1cccc2c1N1[C@H](C)CNC(=O)[C@@H]1C2 | null | 96.5 | null |
99,619 | ord_dataset-10360c60962940178e4bf05e54b1655c | null | 1982-01-01T00:10:00 | true | Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.C([OH:15])C>>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2](=[O:15])[S:3][C:4]=2[CH:10]=1 | Clc1ccc2nc(Cl)sc2c1 | CCO | null | Cl | 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 | 4.081 gm (0.02 mol) of 2,6-dichloro-benzothiazole were refluxed for 4 hours in 100 ml of a mixture of equal parts of ethanol and concentrated hydrochloric acid. After distilling the reaction mixture with 100 ml of water, the resulting precipitate was filtered off and washed thoroughly with water. For further purificati... | O=c1[nH]c2ccc(Cl)cc2s1 | null | null | null |
923,482 | ord_dataset-cc0899cd744f4f7f8e7f2463560faad1 | null | 2009-01-01T00:12:00 | true | [O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]([C:13]([OH:15])=O)[CH2:4][N:3]1[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])(=[O:18])=[O:17].[CH3:29][C:30]1[C:31]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[N:32][C:33]([CH3:36])=[CH:34][N:35]=1>>[CH3:29][C:... | O=C(O)C1CN(S(=O)(=O)c2ccccc2C(F)(F)F)C(=O)N1c1ccccc1 | Cc1cnc(C)c(N2CCNCC2)n1 | 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 | null | null | In analogy to example 1, (RS)-2-oxo-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidine-4-carboxylic acid (example 11) was coupled with 3′,6′-dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (CAS [59215-42-8]) to give the title compound as a colorless solid. MS: 589.0 ([M+H]+) | Cc1cnc(C)c(N2CCN(C(=O)C3CN(S(=O)(=O)c4ccccc4C(F)(F)F)C(=O)N3c3ccccc3)CC2)n1 | null | null | null |
1,468,247 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)[CH3:15])=[CH:4][CH:3]=1.Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:16]2[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]2)[... | CC(c1ccccc1-c1ccc(Cl)cc1)N1CCC2(CC1)OCCO2 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 85 | null | To a solution of 8-[1-(4′-Chloro-biphenyl-2-yl)-ethyl]-1,4-dioxa-8-aza-spiro[4.5]decane (3.1 g, 8.66 mmol) in dioxane-water (1:1 60 mL) is added HCl 37% (10.5 mL, 346 mmol). The reaction is then heated up to 85° C. for 26 hours. The solvent is then removed under vacuum and the aqueous phase is basified to pH=9 using so... | CC(c1ccccc1-c1ccc(Cl)cc1)N1CCC(=O)CC1 | null | null | null |
578,392 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | C([Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[CH:21][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.[CH3:30][N:31]1[CH:35]=[C:34]([S:36]([N:39]2[CH2:44][CH2:43][CH:42]([CH2:45][NH2:46])[CH2:41][CH2:40]2)(=[O:38])=[O:37])[N:33]=[CH:32]1>>[OH:28][C@@H:27]([CH2:29][NH:46][CH2:45][CH:42]1[C... | CC(C)(C)[Si](Oc1ccc(OC[C@@H]2CO2)cc1)(c1ccccc1)c1ccccc1 | Cn1cnc(S(=O)(=O)N2CCC(CN)CC2)c1 | 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 | null | null | Prepared from t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane (0.404 g, 1.0 mmol) and [1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-ylmethyl amine (0.650 g, 1.8 mmol) according to the procedure used in example 37 to give 0.045 g of the title compound as a white solid. | Cn1cnc(S(=O)(=O)N2CCC(CNC[C@H](O)COc3ccc(O)cc3)CC2)c1 | null | 10.6 | null |
691,645 | ord_dataset-6214af00a7eb47f3887ef21a94320a7e | null | 2005-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10](SC)[N:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[C:16]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][N:17]=1.[F:23][C:24]1[C:25]([Sn](CCCC)(CCCC)CCCC)=[N:26][CH:27]=[C:28]([F:30])[CH:29]=1>>[F:23][C:24]1[C:25]([C:10]2[N:11]=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:16... | CSc1nncc(-c2ccc(F)c(-c3ncccc3F)c2)n1 | CCCC[Sn](CCCC)(CCCC)c1ncc(F)cc1F | 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 | null | null | A solution of 5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-3-methylsulfanyl-[1,2,4]triazine and 3, 5-difluoro-2-tributylstannylpyridine were coupled together by the method of Example 36 to give 3-(3,5-difluoro-pyridin-2-yl)-5-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]-[1,2,4]triazine: δH (500 MHz, CDCl3) 7.34 (1H, m), 7.... | Fc1cnc(-c2nncc(-c3ccc(F)c(-c4ncccc4F)c3)n2)c(F)c1 | null | null | null |
482,179 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]3)C(=O)C2=CC=CC=C12.O.NN.Cl>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]2 | O=C1c2ccccc2C(=O)N1CCCOc1ccc2[nH]c(=O)ccc2c1 | null | null | Cl | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | 1 | To a suspension of 6-(3-phthalimidopropoxy)carbostyril (300 g) in ethanol (3 liters) is added hydrazine monohydrate (46 g), and the mixture is refluxed for 8 hours. After the mixture is allowed to cool, the precipitated crystals are collected by filtration, suspended in water, and the suspension thus obtained is acidif... | NCCCOc1ccc2[nH]c(=O)ccc2c1 | null | 74.5 | null |
717,778 | ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | null | 2006-01-01T00:07:00 | true | [F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([CH2:23][NH:24][C:25]([CH:27]5[CH2:29][CH2:28]5)=[O:26])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][N:8]2... | O=C(NCc1ccc2c(c1)N(C1CCN(CCc3ccc(F)cc3)CC1)CC2)C1CC1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-cyclopropanecarboxamidomethylindoline (90 mg) obtained in Example 159, activated manganese dioxide (450 mg) and chloroform (10 ml) were treated as in Example 285 to give the title compound (60 mg) as a white powder (yield: 73%). | O=C1CCCN1Cc1ccc2ccn(C3CCN(CCc4ccc(F)cc4)CC3)c2c1 | null | 67 | null |
1,610,792 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11](O)([CH3:13])[CH2:10][C@H:9]1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:33])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:33])([CH3:13])[CH2:10][C@H:9]1[C:15](=[... | CCN(CC)S(F)(F)F | CC(C)(C)OC(=O)N1C[C@@](C)(O)C[C@H]1C(=O)NCc1cccc(Cl)c1F | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 1 | To a solution of (2S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (865 mg, 2.1 mmol) in CH2Cl2 (60 mL) under nitrogen at −78° C. was added DAST (550 μL, 4.16 mmol) and the solution was slowly allowed to reach RT and stirred for 1 h. The reaction mixture was... | CC(C)(C)OC(=O)N1C[C@](C)(F)C[C@H]1C(=O)NCc1cccc(Cl)c1F | null | null | null |
80,984 | ord_dataset-f196f0a87dd74fcd82ca019f8ff5cf9c | null | 1981-01-01T00:05:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:16])=[CH:4][C:3]=1[O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1 | O=C1CCC(=O)N1Br | Cc1ccc(F)c(Oc2ccccc2)c1 | null | CC(C)(C#N)N=NC(C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | For example, 4-fluoro-3-phenoxy-toluene, when reacted with N-bromosuccinimide in the presence of a radical initiator, for example azodiisobutyronitrile, optionally using a diluent, for example carbon tetrachloride, optionally using a diluent, and 100° C., gives 4-fluoro-3-phenoxy-benzyl bromide. From this, 4-fluoro-3-p... | Fc1ccc(CBr)cc1Oc1ccccc1 | null | null | null |
506,460 | ord_dataset-631d58dab387485c8eb0db4c20a232b7 | null | 2001-01-01T00:06:00 | true | [F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:7]2[OH:17].[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:19])[CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17] | O=C([O-])[O-] | CCOC(=O)c1cnc2c(F)cc(I)cc2c1O | null | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CI | CN(C)C=O | null | null | null | null | null | null | null | null | null | 95 | 8 | Ethyl 8-fluoro4-hydroxy-6-iodo-3-quinolinecarboxylate (18.1 g) prepared as an intermediate in Preparation No. 1 is dissolved in DMF (430 mL), and K2CO3 (36.1 g, 261 mmol) and methyl iodide (3.25 mL, 52.3 mmol) are added. The reaction mixture is heated to 95° C. for 6 h, then allowed to stir at room temperature overnigh... | CCOC(=O)c1cn(C)c2c(F)cc(I)cc2c1=O | null | 84 | null |
1,079,762 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]([C:9]1([OH:23])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)[OH:8]>CO.[Pd]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]([C:9]1([OH:23])[CH2:12][NH:11][CH2:10]1)[OH:8] | O=C(OCc1ccccc1)N1CC(O)(C(O)CC2OCCO2)C1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | Phenylmethyl 3-[2-(1,3-dioxolan-2-yl)-1-hydroxyethyl]-3-hydroxyazetidine-1-carboxylate (235 mg, 0.728 mmol) was dissolved in methanol (5 mL) and treated with 5 wt % palladium on carbon (50 mg) under hydrogen at ambient for 1.5 h. The mixture was filtered and the filtrate was concentrated in vacuo to afford 3-[2-(1,3-di... | OC(CC1OCCO1)C1(O)CNC1 | null | 100.1 | null |
757,229 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [CH3:1][C@@:2]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[C:5](=[O:12])[CH2:4][C:3]2=[O:13].C(N(CC)CC)C.[F:21][C:22]([F:37])([F:36])[C:23]1[CH:24]=[C:25]([N:33]=[C:34]=[O:35])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1.Cl>CN(C)C1C=CN=CC=1.ClCCl>[F:21][C:22]([F:36])([F:37])[C:23]1[CH:24]=[C:25]([NH:33][... | O=C=Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC1(C)C2CC[C@]1(C)C(=O)CC2=O | null | CN(C)c1ccncc1 | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | 30 | 8 | To an ice-cooled solution of (1S)-1,8,8-trimethylbicyclo[3.2.1]octane-2,4-dione (0.36 g, 2.0 mmole), triethylamine (0.20 g, 2.0 mmole) and 4-(dimethylamino)pyridine (0.24 g, 2.0 mmole) in dry dichloromethane (25 mL) was added a solution of 3,5-bis-(trifluoromethyl)phenyl isocyanate (0.51 g, 2.0 mmole) in dry dichlorome... | CC1(C)C2CC[C@]1(C)C(=O)C(C(=O)Nc1cc(C(F)(F)F)cc(C(F)(F)F)c1)C2=O | null | 41.3 | null |
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