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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,155,026 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9](I)[S:8][C:6]=2[N:7]=1.[CH3:18][S:19]([NH:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)(=[O:21])=[O:20]>>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[N:10]=[C:9]([C:27]3[CH:28]=[C:23]([NH... | CS(=O)(=O)Nc1cccc(B(O)O)c1 | Clc1nc(N2CCOCC2)c2nc(I)sc2n1 | null | null | null | null | null | null | null | 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-(5-Chloro-2-iodothiazolo[5,4-d]pyrimidin-7-yl)morpholine 18 was reacted with 3-(methylsulfonylamino)phenylboronic acid via General Procedure A to give crude 3-(5-chloro-7-morpholinothiazolo[5,4-d]pyrimidin-2-yl)-N-methylsulfonylbenzenamine, which was then reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)py... | CS(=O)(=O)Nc1cccc(-c2nc3c(N4CCOCC4)nc(Cl)nc3s2)c1 | null | null | null |
1,706,678 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@:8]2([CH2:27][F:28])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH:18]C(=O)C3C=CC=CC=3)=[N:9]2)[CH:7]=1.N12CCCN=C1CCCCC2>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C@:8]2([CH2:27][F:28])[CH2:13][C@@H:12]([C:14]([F:17])([F:15])[F:16])[O:11][C:10]([... | Nc1ccc(F)c([C@]2(CF)C[C@@H](C(F)(F)F)OC(NC(=O)c3ccccc3)=N2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCC2=NCCCN2CC1 | CO | null | null | null | null | null | null | null | null | null | 80 | null | A microwave vial was charged with a solution of crude N-((4S,6S)-4-(5-amino-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (1k, 0.561 g, 1.357 mmol, Example 1 step 9) in MeOH (9 mL). 1,8-diazabicyclo[5.4.0]undec-7-ene (1.653 g, 10.86 mmol, Aldrich) was added and the vial w... | NC1=N[C@](CF)(c2cc(N)ccc2F)C[C@@H](C(F)(F)F)O1 | null | 82.2 | null |
1,322,889 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Cl[C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=3)[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[N:30]1([C:36]([NH2:38])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[Cl:21][C:15]1[CH:14]=[C:13]2[C:18]... | NC(=O)N1CCNCC1 | O=C(NCc1cn(-c2ccccc2)c2cc(Cl)ccc2c1=O)c1ccc(Cl)nc1 | null | null | null | null | null | null | null | 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-{5-[(7-Chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-carbamoyl]-pyridin-2-yl}-piperazine-1-carboxylic acid amide was prepared starting from intermediate E and piperazine-1-carboxylic acid amide. MS calcd. for C27H25ClN6O3 [(M+H)+] 517.2, obsd. 517.0. | NC(=O)N1CCN(c2ccc(C(=O)NCc3cn(-c4ccccc4)c4cc(Cl)ccc4c3=O)cn2)CC1 | null | null | null |
226,647 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)=[CH:4][CH:3]=1.[C@@H:23]12[C:32](=[O:33])[O:31][C:29](=[O:30])[C@@H:24]1[CH2:25][CH2:26][CH2:27][CH2:28]2>C(OCC)C>[C:19]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2... | CC(C)(C)c1cc(-c2ccc(N)cc2)cc(C(C)(C)C)c1O | O=C1OC(=O)[C@@H]2CCCC[C@H]12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | null | 16 | To a solution of 2.97 g of 4'-amino-3,5-di-t-butyl-4-hydroxybiphenyl in 200 ml of diethyl ether was added a solution of 1.54 g (0.01 mole) of cis-1,2-cyclohexanedicarboxylic anhydride in 75 ml of diethyl ether, and the resulting solution was stirred for about 16 hours. A solid was removed by filtration, rinsed with die... | CC(C)(C)c1cc(-c2ccc(NC(=O)[C@H]3CCCC[C@H]3C(=O)O)cc2)cc(C(C)(C)C)c1O | null | 70.3 | null |
706,603 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=O.O.[CH3:27][N:28](C)C=O>CN.C(O)C>[CH3:27][NH:28][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[C... | CN(C)C=O | COC(=O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | 48 | 300 mg (0.87 mmol) (RS)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester is dissolved in a mixture of 1 ml N,N-dimethylformamide and 0.18 ml of a 33% solution of methylamine in ethanol. The reaction vessel is tightly stopped and hold at 120° C. for 48 hours. Water is added and the prod... | CNC(=O)C1CC(=O)N(c2ccc(OCc3cccc(F)c3)cc2)C1 | null | null | null |
102,784 | ord_dataset-bdb961f26fac426eaa2de8f54a284acf | null | 1983-01-01T00:02:00 | true | [C:1]([NH:9][C:10](=[N:13][CH3:14])SC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24]>>[C:1]([NH:9][C:10]([NH:13][CH3:14])=[N:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[C... | CN=C(NC(=O)c1ccccc1)SC | NCCCCCCCCN | null | null | null | null | null | null | null | 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 mixture of N-benzoyl-N'-methyl-S-methylisothiourea and an excess of 1,8-diaminooctane is maintained at 60° for 5 hours to give a solid product which is washed with ether to leave N-benzoyl-N'-methyl-N"-(8-aminooctyl)guanidine. | CNC(=NCCCCCCCCN)NC(=O)c1ccccc1 | null | null | null |
1,081,812 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | [F:1][C:2]([F:20])([F:19])[C:3]1[N:7]2[N:8]=[C:9]([N:12]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Br[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26]>>[OH:18][C:15]1([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])[CH2:16][CH2:17][N:12]([C:9]2[CH:10]=[C... | O=C1CCN(c2ccc3nnc(C(F)(F)F)n3n2)CC1 | N#Cc1cccc(Br)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 | A mixture of 1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-one and 3-bromobenzonitrile was allowed to react by the method of Example 315 to give 3-[4-hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]benzonitrile in 26% yield. | N#Cc1cccc(C2(O)CCN(c3ccc4nnc(C(F)(F)F)n4n3)CC2)c1 | null | 26 | null |
163,926 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | Cl[C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:20][O-:21].[Na+]>>[OH:19][CH:16]([CH2:17][OH:18])[CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([O:21][CH3:20])[C:11]=2[N:12]=[CH:13]1 | OCC(O)Cn1cnc2c(Cl)nc3ccccc3c21 | C[O-] | null | [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 | null | Using the method of Example 157, 4-chloro-1-(2,3-dihydroxypropyl)-1H-imidazo[4,5-c]quinoline (from Example 124, Part D) was reacted with sodium methoxide to provide 1-(2,3-dihydroxypropyl)-4-methoxy-1H-imidazo[4,5-c]quinoline, m.p. 214°-216° C. after recrystallization from isopropanol. Analysis: Calculated for C14H15N3... | COc1nc2ccccc2c2c1ncn2CC(O)CO | null | null | null |
1,070,049 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [CH:1]1([CH2:4][CH2:5][O:6][C:7]2[N:15]=[C:14]3[C:10]([N:11]=[C:12]([O:23]C)[N:13]3[CH2:16][CH2:17][CH:18]3[CH2:22][CH2:21][CH2:20][O:19]3)=[C:9]([NH2:25])[N:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>CO>[NH2:25][C:9]1[N:8]=[C:7]([O:6][CH2:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:23])[N:13]2[CH2:16... | COc1nc2c(N)nc(OCCC3CC3)nc2n1CCC1CCCO1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | C1COCCO1 | null | null | null | null | null | null | null | null | null | 25 | 16 | To a solution of 2-[(2-cyclopropylethyl)oxy]-8-(methyloxy)-9-[2-(tetrahydro-2-furanyl)ethyl]-9H-purin-6-amine (88 mg, 0.253 mmol) in methanol (10 ml) at room temperature was added 4M HCl in 1,4 dioxane (2.106 ml, 8.42 mmol) to give a pale straw coloured solution. The reaction mixture was stirred at ambient temperature ... | Nc1nc(OCCC2CC2)nc2c1[nH]c(=O)n2CCC1CCCO1 | null | 48.6 | null |
1,378,621 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [Li+].[BH4-].[F:3][C:4]1([F:26])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:10]=2)[C@H:6]([C:22](OC)=[O:23])[CH2:5]1>C1COCC1.C(OCC)(=O)C>[F:26][C:4]1([F:3])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]([F:20])([F:21])[F:19])... | COC(=O)[C@@H]1CC(F)(F)CN1c1ccc([N+](=O)[O-])c(C(F)(F)F)c1 | null | null | [BH4-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 0 | 0.33 | To a suspension of LiBH4 (55 mg, 2.54 mmol) in anhydrous THF (3 mL) was added a solution of (S)-methyl 4,4-difluoro-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine-2-carboxylate (300 mg, 0.85 mmol) in anhydrous THF at 0° C. The reaction mixture was stirred at 0° C. for 20 min then allowed to come to room temperature a... | O=[N+]([O-])c1ccc(N2CC(F)(F)C[C@H]2CO)cc1C(F)(F)F | null | null | null |
600,589 | ord_dataset-82e842e611ef4a05b6e7f9ea0a46d52d | null | 2003-01-01T00:07:00 | true | [CH3:1][O:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]O.C(N(CC)C(C)C)(C)C.S(Cl)([Cl:26])=O>C(OCC)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][Cl:26] | O=S(Cl)Cl | COCOc1c(CO)cccc1OC | 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 | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.25 | 2.34 g (11.8 mmol) of 2-methoxymethoxy-3-methoxybenzyl alcohol was dissolved in 20 ml of diethyl ether, and the resultant solution was added with 1.53 g (11.8, mmol) of N,N-diisopropylethylamine. To the obtained solution was fed dropwise 1.40 g (11.8 mmol) of thionyl chloride and diethyl ether (15 ml) in a manner of sp... | COCOc1c(CCl)cccc1OC | null | null | null |
80,083 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].[CH2:12]=[S:13]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]=[C:12]=[S:13] | C=S | Nc1cc([N+](=O)[O-])ccc1Cl | 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 | A mixture of 50 parts of 2-chloro-5-nitrobenzenamine, 33.4 parts of methanethial and 450 parts of 1,4-dioxane is stirred and refluxed for 4 hours. The reaction mixture is evaporated, yielding 62.2 parts of 1-chloro-2-isothiocyanato-4-nitrobenzene as a residue. | O=[N+]([O-])c1ccc(Cl)c(N=C=S)c1 | null | null | null |
625,691 | ord_dataset-e44331dc51de453ca14b7032593c1958 | null | 2004-01-01T00:02:00 | true | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([N:13](C1C=CC=CC=1)[C@H:14]([C:16]([NH:18][C@H:19]([CH:24]=[O:25])[CH2:20][C:21]([OH:23])=[O:22])=[O:17])[CH3:15])=[O:12].C=O.[C:34](O)(=O)[CH3:35]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][C@H:14]([C:... | CC(=O)O | C[C@@H](C(=O)N[C@H](C=O)CC(=O)O)N(C(=O)c1cc2ccccc2n1C)c1ccccc1 | null | C=O | 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 | (3S)-3-[(1-Methylindole-2-carbonyl)phenyl-alaninyl]amino-4-oxobutanoic acid, semicarbazone (116 mg, 0.25 mmol) were dissolved in methanol (3 mL), formaldehyde (1 mL, 37% wt. aq) and acetic acid (1 mL) and the resulting solution was stirred for 9 hours under a nitrogen atmosphere at room temperature. The reaction mixtur... | Cn1c(C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H](C=O)CC(=O)O)cc2ccccc21 | null | 25 | null |
1,702,782 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([C:9]1[N:17]2[C:12]([CH2:13][O:14][CH2:15][CH2:16]2)=[C:11]([C:18]([OH:20])=O)[CH:10]=1)=[O:8].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:43]1([C@H:49]([NH2:52])[CH2:50][CH3:51])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C)C=O.O>[C:43]1([C@H:49]([NH:52][C:18]([C:11]2[CH:1... | C[C@H]1CCCN1C(=O)c1cc(C(=O)O)c2n1CCOC2 | CC[C@@H](N)c1ccccc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | 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 | 50 | 1.5 | To a solution of 6-((S)-2-methyl-pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid (Comp. No. 7c) (300 mg, 0.914 mmol) in dimethylformamide (4 ml) was added 1-hydroxybenzotriazole (136 mg, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (193 mg, 1 mmol). The mix... | CC[C@@H](NC(=O)c1cc(C(=O)N2CCC[C@@H]2C)n2c1COCC2)c1ccccc1 | null | 67 | null |
610,339 | ord_dataset-73916d628db147c89020b3baac642d48 | null | 2003-01-01T00:09:00 | true | [Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[N:28](COCC3C=CC=CC=3)[C:26]2=[O:27])[C@H:22]([O:43][CH2:44][CH2:45][OH:46])[C@@H:21]1[OH:47])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd]>[Si:1]... | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCO)c(=O)n(COCc2ccccc2)c1=O | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5′-O-t-Butyldiphenylsilyl-3-benzyloxymethyl-2′-O-(hydroxyethyl)-5-methyluridine prepared in Example 31 above is hydrogenated using 10% Pd on carbon as per the procedure of Example 35 above to give the title compound. | Cc1cn([C@@H]2O[C@H](CO[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[C@@H](O)[C@H]2OCCO)c(=O)[nH]c1=O | null | null | null |
514,109 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>C(OCC)(=O)C>[C:14]([NH:18][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15] | O=C(Cl)c1ccc2ccccc2c1 | CC(C)(C)N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 1 above and using 2-naphthoyl chloride and tert-butylamine (and ethyl acetate in place of benzene), the title compound was prepared as a white solid, m.p. 154.8-159.2° C. | CC(C)(C)NC(=O)c1ccc2ccccc2c1 | null | null | null |
1,389,523 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[F:24])[CH2:5][CH2:6][C:7]1[NH:8][CH:9]=[C:10]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)[C:11](=[O:13])[N:12]=1.[Cu][C:26]#[N:27]>CN1C(=O)CCC1>[F:24][C:23]1[CH:22]=[CH:21][C:4]([CH2:5][CH2:6][C:7]2[NH:8][CH:9]=[C:10]([CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[N:19][CH:... | N#C[Cu] | O=c1nc(CCc2ccc(F)c(Br)c2)[nH]cc1Cc1cncnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCCC1=O | null | null | null | null | null | null | null | null | null | null | 200 | null | A mixture of 2-(3-bromo-4-fluorophenethyl)-5-(pyrimidin-5-ylmethyl)pyrimidin-4(1H)-one (1.5 g, 3.7 mmol), copper(I) cyanide (399 mg, 4.4 mmol) in NMP (5 mL) was heated with a microwave reactor at 200° C. for 1.5 h. After cooling to room temperature, the mixture was filtered. The filtrate was partitioned between ethyl a... | N#Cc1cc(CCc2nc(=O)c(Cc3cncnc3)c[nH]2)ccc1F | null | 80.6 | null |
472,755 | ord_dataset-cd531114850e4f239b2a3661044ae672 | null | 2000-01-01T00:08:00 | true | [CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]2[N:10]=[C:11]([CH3:24])[N:12]=[C:13]([NH:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:8]=2[N:7]=[N:6]1.[H-].[Na+].[CH2:27](I)[CH3:28]>CN(C)C=O.O>[CH2:27]([N:14]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[CH3:23])[C:13]1[C:8]2[N:... | COCCn1nnc2c(Nc3c(C)cc(C)cc3C)nc(C)nc21 | CCI | null | [H-] | [Na+] | null | 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 | 25 | 48 | The product from Example 38, Part B (150 mg, 0.46 mmol) was treated with sodium hydride (17 mg, 0.55 mmol, 80%) and ethyl iodide (55 ml, 0.69 mmol) in dry dimethylformamide (3 ml) and stirred at room temperature for 48 h. The reaction was diluted with 50 ml water, and extracted with 4-30 ml methylene chloride. The comb... | CCN(c1c(C)cc(C)cc1C)c1nc(C)nc2c1nnn2CCOC | null | null | null |
1,526,018 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[CH2:8]1)[CH2:6][C:5]2=O.[C:20](=[N:26][Si](C)(C)C)=[N:21][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:16](=[CH:17][CH:18]=1)[O:15][C:7]1([CH2:11][CH2:10][CH:9]([CH:12]([CH3:14])[CH3:13])[... | CC(C)C1CCC2(CC(=O)c3cc(Br)ccc3O2)C1 | C[Si](C)(C)N=C=N[Si](C)(C)C | null | Cl[Ti](Cl)(Cl)Cl | null | 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 | 0 | 1 | To a solution of 6-bromo-3′-isopropylspiro[chroman-2,1′-cyclopentan]-4-one (250 mg, 0.776 mmol) in DCM (10 mL) was added TiCl4 (1.55 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.38 mL, 1.707 mmol) was added dropwise. Th... | CC(C)C1CCC2(CC(=NC#N)c3cc(Br)ccc3O2)C1 | null | 92.8 | null |
865,208 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | Br[C:2]1[N:10]([CH2:11][C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[C:9]2[C:8](=[O:20])[N:7]([CH3:21])[C:6](=[O:22])[N:5]([CH3:23])[C:4]=2[N:3]=1.[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.O>CS(C)=O>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([F:18])[C:12]=1[CH2:11][N:10]1[C:9]2[C:8](=[O:20])[N:7]([CH3:2... | C1CCNC1 | Cn1c(=O)c2c(nc(Br)n2Cc2c(F)cccc2Cl)n(C)c1=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CS(C)=O | null | null | null | null | null | null | null | null | null | 130 | 0.5 | A solution of 8-bromo-7-(2-chloro-6-fluorobenzyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (50 mg, 0.12 mmol) in 300 μL DMSO was treated with pyrrolidine (55 μL, 0.55 mmol) and heated at 130° C. for 15 h. The reaction was cooled to 25° C. and treated with 1 mL H2O. After centrifugation for 1 h the liquid was decant... | Cn1c(=O)c2c(nc(N3CCCC3)n2Cc2c(F)cccc2Cl)n(C)c1=O | null | 102.1 | null |
1,356,628 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | O[C:2]1([CH3:18])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=O)[NH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH3:18][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]1=2 | CC1(O)c2ccccc2NC(=O)c2ccccc21 | null | null | [Al+3] | [H-] | [Li+] | 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 | 105 | 0.5 | 11-Hydroxy-11-methyl-5,11-dihydro-dibenzo[b,e]azepin-6-one (3) (51.6 g 0.22 mol) was added to a suspension of LiAlH4 (33 g, 0.88 mol) in dioxane (850 mL). The reaction mixture was heated to 105° C. After 2.5 h under reflux the reaction mixture was cooled, the excess LiAlH4 was destroyed with aqueous Na2SO4 (55 mL). eth... | CC1c2ccccc2CNc2ccccc21 | null | 60.8 | null |
1,087,584 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([O:17]CC=C)=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH-].[Na+]>C(O)C.O>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([OH:17])=[... | C=CCOC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)OC(C)(C)C | null | null | [Na+] | [OH-] | 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 | null | According to the general saponification procedure, 6.11 g crude Boc-D-Leu-Leu-OAllyl were saponified with 3 g sodium hydroxide in ethanol/water to yield 5.0 g crude Boc-D-Leu-Leu-OH which was used in the next step without purification | CC(C)C[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)OC(C)(C)C)C(=O)O | null | 91.4 | null |
836,748 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[N:5]=[C:4]([NH2:16])[N:3]=1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=3[CH3:15])[N:5]=[C:4]([NH2:16])[N:... | Cc1ccc(Cl)cc1-c1cc(Cl)nc(N)n1 | Nc1ccc(Br)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 | Following the method described in Example 26, 4-chloro-6-(5-chloro-2-methyl-phenyl)-pyrimidin-2-yl-amine and 4-bromoaniline provided the title compound (84% yield). 1H NMR (DMSO-d6) δ 2.35 (s, 3H, CH3), 6.10 (s, 1H, Ar), 6.45 (s, 2H, NH2), 7.31 (d, 1H, J=8.3 Hz, Ar), 7.37 (dd, 1H, J=8.2 Hz, J=2.3 Hz, Ar), 7.41 (d, 1H, ... | Cc1ccc(Cl)cc1-c1cc(Nc2ccc(Br)cc2)nc(N)n1 | null | 84 | null |
1,652,298 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [ClH:1].C(OC(=O)[NH:8][C@H:9]1[CH2:12][C@H:11]([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]([CH3:22])[C:14]2=[O:23])[CH2:10]1)(C)(C)C>O1CCOCC1>[ClH:1].[NH2:8][C@H:9]1[CH2:12][C@H:11]([N:13]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]([CH3:22])[C:14]2=[O:23])[CH2:10]1 | Cn1c(=O)n([C@H]2C[C@H](NC(=O)OC(C)(C)C)C2)c2ncccc21 | null | null | Cl | 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 | 25 | 21 | Hydrogen chloride, 4.0M solution in 1,4-dioxane (130 mL, 519 mmol) was added to a stirred solution of the tert-butyl(trans-3-(1-methyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate product of step 2 (33.1 g, 104 mmol) in 1,4-dioxane (400 mL). The reaction mixture was stirred at room temperature for 21 h.... | Cn1c(=O)n([C@H]2C[C@H](N)C2)c2ncccc21 | null | 51 | null |
764,841 | ord_dataset-7a8649d55889427e85b208ae89475895 | null | 2007-01-01T00:04:00 | true | [CH:1]1([C:7]2[CH:41]=[CH:40][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[C:21]([C:24]([O:26]C)=[O:25])[CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:28]([C:31]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)=[O:32])=[CH:29][CH:30]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl... | COC(=O)c1ccc2c(c1)N(C(=O)c1ccc(C3CCCCC3)cc1)Cc1ccc(C(=O)N3CCN(C)CC3)n1C2 | null | 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 | 8 | To a solution of the methyl 10-(4-cyclohexylbenzoyl)-3-[(4-methyl-1-piperazinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-8-carboxylate of Example 1, Step D (1.1 g, 1.93 mmol) in ethanol (10 mL) was added 2.5 N sodium hydroxide (1.5 equiv.) and the reaction mixture was stirred overnight at room tempe... | CN1CCN(C(=O)c2ccc3n2Cc2ccc(C(=O)O)cc2N(C(=O)c2ccc(C4CCCCC4)cc2)C3)CC1 | null | null | null |
1,716,472 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [NH2:1][C:2]1[S:3][C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:5][N:6]=1.[C:11]([NH:14][C:15]1[CH:24]=[CH:23][C:18]([S:19](Cl)(=[O:21])=[O:20])=[CH:17][CH:16]=1)(=[O:13])[CH3:12].Cl>N1C=CC=CC=1>[C:7]([C:4]1[S:3][C:2]([NH:1][S:19]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:11](=[O:13])[CH3:12])=[CH:24][CH:23]=2)(=[O:21])=[O:20... | CC(C)(C)c1nnc(N)s1 | CC(=O)Nc1ccc(S(=O)(=O)Cl)cc1 | null | Cl | 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 | 95 | 1 | 2-Amino-5-tert-butyl-1,3,4-thiadiazole (1.0 g, 6.36 mmol) was suspended in pyridine (1.6 mL). N-Acetylsulfanilyl chloride (1.9 g, 5.1 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred for 1 h. The reaction mixture was then added to aqueous 3N HCl and the mixture extracted wi... | CC(=O)Nc1ccc(S(=O)(=O)Nc2nnc(C(C)(C)C)s2)cc1 | null | 84.3 | null |
245,262 | ord_dataset-5eb2900a93c842ee98f26c305e657b61 | null | 1992-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:15])([F:14])[F:13])[C:5]([NH2:7])=O>O=S(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([F:13])([F:14])[F:15])[C:5]#[N:7] | NC(=O)c1ccc(OC(F)(F)F)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 85 | null | 750 ml of SOCl2 were added to 239.5 g (1 mol) of 3-chloro-4-trifluoromethoxybenzamide and the mixture was heated slowly (corresponding to the evolution of gas) to 85° C. The mixture was then fractionally distilled and 189 g of product having a boiling point at 13 mbar of 96° C. and a melting point of 38° to 40° C. were... | N#Cc1ccc(OC(F)(F)F)c(Cl)c1 | null | 85 | null |
1,344,447 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [I:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C>[I:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:4]=2[N:5]=[CH:6][N:7]=1 | Ic1ncnc2[nH]ccc12 | C[Si](C)(C)CCOCCl | null | [H-] | [Na+] | 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 | null | 610 mg (2.49 mmol) of 4-iodo-7H-pyrrolo[2,3-d]pyrimidine was dissolved in 2.5 mL DMF. 110 mg (2.74 mmol) of 60% sodium hydride was added followed by 480 μL (2.74 mmol) of trimethylsilylethoxymethyl chloride. Yield: 750 mg of an oily product, 90% pure. | C[Si](C)(C)CCOCn1ccc2c(I)ncnc21 | null | null | null |
994,532 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [C:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[Cl:25][S:26](O)(=[O:28])=[O:27]>>[F:21][C:20]([F:23])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:1]3[CH:2]=[CH:3][... | O=S(=O)(O)Cl | FC(F)(F)c1ccc(-c2ccnc(Nc3ccccc3)n2)cc1 | null | null | 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 | A solution of N-phenyl-4-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine (0.16 g, 0.5 mmol) in 1.5 ml of chlorosulfonic acid is stirred at 65 to 70° C. for 1 hr. It is then cooled to room temperature, and added slowly to a stirred mixture of ice and water. The resulting suspension is filtered, and the precipitate is washe... | O=S(=O)(Cl)c1ccc(Nc2nccc(-c3ccc(C(F)(F)F)cc3)n2)cc1 | null | null | null |
364,011 | ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | null | 1997-01-01T00:05:00 | true | Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]2[CH:8]=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1.[CH2:15]1[CH2:24][O:23][C:22]2[CH:21]=[CH:20][C:19]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:18][C:17]=2[O:16]1.[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:33]>C(OCC)(=O)C>[C:31]([OH:36])(=[O:35])[C:32]([OH:34])=[O:... | ClCCCOc1cccc2[nH]ccc12 | c1cc2c(cc1C1CCNCC1)OCCO2 | null | O=C(O)C(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in similar fashion from 1-chloro-3-(1H-indole-4-oxy)propane and 4-(3,4-ethylenedioxyphenyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 59% overall yield as a foam. FDMS m/e=392 (M+ of free bas... | c1cc(OCCCN2CCC(c3ccc4c(c3)OCCO4)CC2)c2cc[nH]c2c1 | null | null | null |
1,485,412 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][NH:16][C:17](=[O:20])[CH2:18]Cl)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:14][CH2:18][C:17](=[O:20])[NH:16][CH2:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=C(CCl)NCC1(O)CCN(Cc2ccccc2)CC1 | null | null | CC(C)(C)[O-] | [K+] | 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 | 25 | 0.67 | To a mixture of compound 398 (41.9 g, 141 mmol) in tetrahydrofuran (300 mL) was added potassium tert-butoxide (31.8 g, 283 mmol), portionwise over 40 minutes. After 3.5 hours of stirring at room temperature, the reaction was concentrated in vacuo. The residue was diluted with DCM and water, and then neutralized with 3N... | O=C1COC2(CCN(Cc3ccccc3)CC2)CN1 | null | 62.1 | null |
1,044,600 | ord_dataset-dd320ded4b3f4764af39de99491533f7 | null | 2011-01-01T00:04:00 | true | [H-].[Na+].[CH2:3]([O:5][C:6]1[CH:24]=[CH:23][C:9]([CH2:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=3[N:12]=2)=[CH:8][CH:7]=1)[CH3:4].Cl[CH2:26][CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30]>O1CCOCC1>[CH2:3]([O:5][C:6]1[CH:24]=[CH:23][C:9]([CH2:10][C:11]2[N:12]([CH2:26][CH2:27... | CCN(CC)CCCl | CCOc1ccc(Cc2nc3cc([N+](=O)[O-])ccc3[nH]2)cc1 | null | [H-] | [Na+] | 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 | 65 | null | To a small, argon purged flask fitted with a condenser and magnetic stirbar is charged Sodium Hydride (60 wt %, 74 mg, 1.850 mmol) and anhydrous dioxane (5 mL) and stirring begun. A solution of 2-(4-Ethoxy-benzyl)-5-nitro-1H-benzimidazole 42 (550 mg, 1.850 mmol) in anhydrous dioxane (10 mL) was added dropwise to the su... | CCOc1ccc(Cc2nc3ccc([N+](=O)[O-])cc3n2CCN(CC)CC)cc1 | null | 13.6 | null |
217,072 | ord_dataset-67ed03c283094854909157b1038e38e3 | null | 1990-01-01T00:10:00 | true | [H][H].C([SiH](CC)CC)C.[OH:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18][CH:17]=[CH:16][C:15]=2[CH:19]=1.FC(F)(F)C(O)=O>>[OH:10][C:11]1[CH:12]=[CH:13][C:14]2[S:18][CH2:17][CH2:16][C:15]=2[CH:19]=1 | [H][H] | Oc1ccc2sccc2c1 | null | CC[SiH](CC)CC | 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 | Scheme I depicts the preparation of the simplest member (2) of the invention, that is where R4 and R6 are both hydrogen. Triethylsilane is reacted with 5-hydroxybenzothiophene in a suitable solvent, e.g, trifluoroacetic acid (TFA) to yield the 5-hydroxy-2,3-dihydrobenzothiophene. ##STR4## | Oc1ccc2c(c1)CCS2 | null | null | null |
1,142,321 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH:10]=[O:11])[S:7][C:6]=1[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[O:4].[BH4-].[Na+]>O1CCCC1.CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:10][OH:11])[S:7][C:6]=1[NH:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:2... | COC(=O)c1cc(C=O)sc1NC(=O)c1ccc(OC)c(OC)c1 | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.33 | Crude 2-(3,4-dimethoxy-benzoylamino)-5-formylthiophene-3-carboxylic acid methyl ester (35 mg) synthesized by the above process was dissolved in tetrahydrofuran/N,N-dimethylformamide=1/1 (10 ml). Sodium borohydride (22 mg) was added to the solution at room temperature, and the mixture was stirred at that temperature for... | COC(=O)c1cc(CO)sc1NC(=O)c1ccc(OC)c(OC)c1 | null | 99.4 | null |
1,478,566 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH3:1][C@@:2]1([C:18]([F:21])([F:20])[F:19])[CH2:17][N:5]2[C:6](=[O:16])[CH:7]=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[N:9]=[C:4]2[NH:3]1.[Br:22][C:23]1[CH:28]=[C:27]([CH2:29]Br)[CH:26]=[CH:25][C:24]=1[F:31].C(=O)([O-])[O-].[Cs+].[Cs+]>>[Br:22][C:23]1[CH:28]=[C:27]([CH:26]=[CH:25][C:24]=1[F:31])[CH2:29][... | Fc1ccc(CBr)cc1Br | C[C@@]1(C(F)(F)F)Cn2c(nc(N3CCOCC3)cc2=O)N1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | 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 product is prepared according to the procedure described in stage k of Example 1, using 100 mg of (2S)-2-methyl-7-(morpholin-4-yl)-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one (Example 1j) and 106 mg of 2-bromo-4-(bromomethyl)-1-fluorobenzene, replacing the sodium hydride with 214 mg of caesium ... | C[C@@]1(C(F)(F)F)Cn2c(nc(N3CCOCC3)cc2=O)N1Cc1ccc(F)c(Br)c1 | null | null | null |
1,502,451 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[CH3:9][NH:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>>[Br:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[N:10]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:9] | Brc1cccc(Br)c1 | CNC1CCCC1 | null | null | null | null | null | null | null | 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 from 1,3-dibromobenzene and N-methylcyclopentanamine using a similar procedure to that described for D43. LCMS (A): m/z (M+H)+ 254/256, Cl2H16BrN requires 253/255 (acidic). | CN(c1cccc(Br)c1)C1CCCC1 | null | null | null |
1,638,250 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [O:1]([C:8]1[CH:20]=[CH:19][C:11]2[NH:12]C(=O)[NH:14][S:15](=[O:17])(=[O:16])[C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>OS(O)(=O)=O>[NH2:12][C:11]1[CH:19]=[CH:20][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][C:10]=1[S:15]([NH2:14])(=[O:16])=[O:17] | O=C1Nc2ccc(Oc3ccccc3)cc2S(=O)(=O)N1 | null | null | O=S(=O)(O)O | [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 | 105 | null | A mixture of 7-phenoxy-1,1-dioxo-1,4-dihydro-2-H-benzo[1,2,4]thiadiazin-3-one (18.0 g, 61.8 mmol) in aqueous H2SO4 (50% v/v, 1 L) was heated at 105° C. for 7 h. The clear solution was then cooled to 0° C. and neutralized using 5N NaOH. The product was extracted with ethyl acetate. The combined extracts were washed with... | Nc1ccc(Oc2ccccc2)cc1S(N)(=O)=O | null | 24.5 | null |
733,451 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | C(N=C=NC(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:21][C:20](=[N:22][O:23][CH3:24])[CH2:19][C@H:18]1[C:25]([OH:27])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:28](=[N:31]O)([NH2:30])[CH3:29]>C(Cl)Cl.C1COCC1>[CH3:24][O:23][N:22]=[C:20]1[CH2:21][N:17]([C:15]([O:14][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:16])[C@H:18]([C:25]2... | CC(N)=NO | CON=C1C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1 | null | CC(C)N=C=NC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 8 | Diisopropylcarbodiimide (3.16 g, 25.17 mmol) was added to a solution of (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidine-carboxylic acid (Intermediate 2, 6.50 g, 25.17 mmol) and acetamidoxime (Intermediate 7, 1.86 g, 25.17 mmol) in DCM (55 ml) and stirred overnight at room temperature (DCM-insoluble amid... | CON=C1C[C@@H](c2nc(C)no2)N(C(=O)OC(C)(C)C)C1 | null | 59 | null |
1,515,093 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [C:1]([O:5][C:6]([NH:8][CH:9]([CH:21](O)[CH2:22][O:23][Si:24]([CH3:30])([CH3:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:10]([NH:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:11]=[C:10]1[C@@H... | CC(C)(C)OC(=O)NC(C(=O)NOCc1ccccc1)C(O)CO[Si](C)(C)C(C)(C)C | null | 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 | 25 | 2 | A solution of THF (1.5 L) containing 2-[(tert-butoxy)carbonylamino]-3-hydroxy-N-(phenylmethoxy)-4-(1,1,2,2-tetramethyl-1-silapropoxy)butanamide (9.8 g, 21.56 mmol), triphenylphosphine (17.5 g, 66.8 mmol) and diethyl azodicarboxylate (11.26 g, 64.7 mmol) was stirred at room temperature for 2 h. The solvent was evaporate... | CC(C)(C)OC(=O)N[C@@H]1C(=O)N(OCc2ccccc2)[C@@H]1CO[Si](C)(C)C(C)(C)C | null | 77 | null |
66,302 | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | null | 1980-01-01T00:05:00 | true | [NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[C:35]([C:39]1[CH:40]=[C:41]([CH:44]=[C:45]([C:48]([CH3:51])([CH3:5... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N)[C@H]2SC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | A solution of diphenylmethyl 7β-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylate (9.89 g) and 3,5-di-t-butyl-4-hydroxybenzaldehyde (5.62 g) in a mixture of benzene (160 ml) and dichloromethane (40 ml) is refluxed for 1 hour in the presence of a molecular sieve to give a solution of diphenylmethyl 7β... | Cn1nnnc1SCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)[C@@H](N=Cc3cc(C(C)(C)C)c(O)c(C(C)(C)C)c3)[C@H]2SC1 | null | null | null |
1,734,031 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:20]([C:21]([F:24])([F:23])[F:22])=[N:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:25]C)[CH:17]=2)[N:12]=1)[C:5]([OH:7])=[O:6].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[C:20]([C:21]([F:23])([F:24])[F:22])=[N:19][C:18]2[C:13](=[CH:14][C... | COc1ccc2nc(-c3ccc(C(=O)O)cc3Cl)c(C(F)(F)F)nc2c1 | null | null | BrB(Br)Br | null | 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 | 25 | 8 | A mixture of 3-chloro-4-(6-methoxy-3-(trifluoromethyl)quinoxalin-2-yl)benzoic acid (150 mg, 0.392 mmol) and BBr3 (3 mL) in anhydrous DCM (30 mL) was stirred at 25° C. overnight. The resulting mixture was quenched with water (30 mL), extracted with EtOAc (50 mL×3), dried over Na2SO4 and concentrated in vacuo. The residu... | O=C(O)c1ccc(-c2nc3ccc(O)cc3nc2C(F)(F)F)c(Cl)c1 | null | 18 | null |
4,442 | ord_dataset-a5669edbeffe43bf8514c1bfede8f882 | null | 1976-01-01T00:04:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)C.[OH-].[Na+]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2] | Sc1ccccc1 | O=[N+]([O-])c1ccc(Cl)cc1C(F)(F)F | null | [Na+] | [OH-] | 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 | null | A solution of 2-nitro-5-chlorobenzotrifluoride (33.8 g, 0.15 mole), benzenethiol (16.6 g, 0.15 mole) and ethanol (150 ml) is heated to its reflux temperature under nitrogen. To this solution is slowly added a solution of sodium hydroxide (6 g, 0.15 mole) and water (7 ml) at such a rate that refluxing continues with no ... | O=[N+]([O-])c1ccc(Sc2ccccc2)cc1C(F)(F)F | null | null | null |
1,634,117 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C:9]1([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C... | CC(C)(C)OC(=O)N1CCNCC1(C)C | O=Cc1ccccc1 | 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 | O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 2.20 g of 2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester in 50 ml DCM was added 1.15 ml of benzaldehyde, followed by the addition of 2.61 g of sodium triacetoxyborohydride in small portions. The reaction was stirred at r.t. overnight. To the reaction was then added water. The layers were se... | CC(C)(C)OC(=O)N1CCN(Cc2ccccc2)CC1(C)C | null | 100 | null |
1,052,055 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | C(OC(=O)[NH:10][C@H:11]1[CH2:23][C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]#[N:25])[CH:20]=3)[NH:15][C:14]=2[CH2:13][CH2:12]1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][C@@H:11]1[CH2:12][CH2:13][C:14]2[NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:24]#[N:25])=[CH:20][C:21]=3[C:22]=2[CH2:23]1 | N#Cc1ccc2[nH]c3c(c2c1)C[C@H](NC(=O)OCc1ccccc1)CC3 | null | null | [Pd] | 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 | 18 | Combine (R)-(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-carbamic acid benzyl ester (Preparation 62) (7.1 mmol, 2.44 g) in anhydrous ethanol (100 mL). To the stirred solution add 5% palladium/carbon (600 mg). Purge and fill the reaction vessel with hydrogen (3×) and stir the reaction mixture under hydrogen at atmosphe... | N#Cc1ccc2[nH]c3c(c2c1)C[C@H](N)CC3 | null | 48 | null |
1,473 | ord_dataset-a0eff6fe4b4143f284f0fc5ac503acad | null | 1976-01-01T00:01:00 | true | [OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[C:9]([CH3:15])=[C:8]4[CH:16]=[CH:17][N:18]=[CH:19][C:7]4=[C:6]([CH3:20])[C:5]=3[C:4]=2[CH:3]=1.C([O-])(O)=O.[Na+].[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(Cl)(=O)C>[C:26]([O:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[C:9]([CH3:15])=[C:8]4[CH:16]=[CH:17][N:18]=[CH:19][C:7]4=[... | CC(=O)OC(C)=O | Cc1c2ccncc2c(C)c2c1[nH]c1ccc(O)cc12 | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | 0.17 | A solution of 9-hydroxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (10 g.) in acetic anhydride (75 ml.) and acetyl chloride (25 ml.) was stirred at room temperature for 2 hours. The reaction mixture was poured into excess NaHCO3 solution and stirred for 10 minutes. The resulting precipitate was removed by filtration and w... | CC(=O)Oc1ccc2[nH]c3c(C)c4ccncc4c(C)c3c2c1 | null | 75 | null |
1,100,268 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH2:8] | O=[N+]([O-])c1ccc(O)c(Cl)c1 | BrCc1ccccc1 | 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 | null | null | In a 250 mL flask equipped with a reflux condenser, 2-chloro-4-nitrophenol 4.65 g (26.6 mmol), benzyl bromide 2.97 mL (27.0 mmol, 1 eq), K2CO3 9.4 g (54 mmol, 2 eq) and DMF (60 mL) were added and then heated to reflux. The procedure was conducted as Example 1, the residue was purified by column chromatography to obtain... | Nc1ccc(OCc2ccccc2)c(Cl)c1 | null | 73 | null |
991,444 | ord_dataset-b6d8835b0c934476a36e6149e7597487 | null | 2010-01-01T00:09:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH:9]2[O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]3[O:34][CH2:33][CH2:32][N:31]([CH2:35][CH2:36][CH2:37][O:38][CH3:39])[C:30]=3[CH:40]=2)=[CH:4][CH:3]=1.I[CH:42]([CH3:44])[CH3:... | COCCCN1CCOc2ccc(COC3CN(C(=O)OCc4ccccc4)CCC3c3ccc(O)cc3)cc21 | CC(C)I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Analogously to Method F, 0.05 g of benzyl 4-(4-hydroxyphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1 carboxylate and 0.0316 g of 2-iodopropane are reacted at 50° C. The title compound is obtained as an orange oil. Rf=0.34 (1:1 EtOAc-heptane). Rt=5.78. | COCCCN1CCOc2ccc(COC3CN(C(=O)OCc4ccccc4)CCC3c3ccc(OC(C)C)cc3)cc21 | null | null | null |
1,252,104 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]>CO.[Pd]>[NH2:12][C:4]1[C:5]([CH3:11])=[C:6]([CH:10]=[C:2]([F:1])[CH:3]=1)[C:7]([OH:9])=[O:8] | Cc1c(C(=O)O)cc(F)cc1[N+](=O)[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 | 25 | 24 | To a solution of (E1) in MeOH (0.5 M), Pd on carbon (10 wt %, 0.2 eq.) was added. The reaction mixture was equipped with H2 atmosphere and the resulting suspension was stirred at RT for 24 h. The precipitated was filtered off and the filtrate was evaporated to dryness to yield the title compound as a brown powder that ... | Cc1c(N)cc(F)cc1C(=O)O | null | null | null |
1,705,918 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CS([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[O:20])[CH2:14][CH2:13]1)(=O)=O>>[CH:1]1([S:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:29... | CS(=O)(=O)N1CCC(NC(=O)Nc2ccc(C(F)(F)F)cc2)CC1 | O=S(=O)(Cl)C1CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cyclopropylsulfonyl chloride (68.5 mg, 0.487 mmol) was reacted with PTU (70 mg, 0.244 mmol) as the same manner as the synthesis of 1-(1-(methylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (65 mg, 0.166 mmol, 68% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.78 (s, 1H), 7.57 (s, 4H), 6.... | O=C(Nc1ccc(C(F)(F)F)cc1)NC1CCN(S(=O)(=O)C2CC2)CC1 | null | 68 | null |
1,582,738 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[C:22]([F:24])[CH:23]=[C:18]3[N:17]([CH:25]([CH3:27])[CH3:26])[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[F:24][C:22]1[CH:23]=[C:18]2[N:17]([CH:25]([CH3:27])[CH3:26])[N:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[C:19]2=[N:20][CH:... | CC(C)n1nc(-c2ccc(OCc3ccccc3)cc2)c2ncc(F)cc21 | null | null | [Pd] | 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 | 1 | A mixture of 3-[4-(benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine (130 mg) and 10% Pd—C (100 mg) in EtOH (20 mL) was stirred at room temperature for 1 h under H2 atmosphere, filtered and evaporated. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title co... | CC(C)n1nc(-c2ccc(O)cc2)c2ncc(F)cc21 | null | 77.9 | null |
876,772 | ord_dataset-e1c3af9b105b4af09a5171403bbfc06f | null | 2009-01-01T00:04:00 | true | [C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:7]([S:8]([NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18]... | COC(=O)c1ccccc1COc1ccc(CCN)cc1 | O=S(=O)(Cl)Cc1ccccc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | 25 | null | Alpha-toluenesulfonyl chloride (38 mg, 0.199 mmol) and methyl 2-{[4-(2-aminoethyl)phenoxy]methyl}benzoate hydrochloride (64 mg, 0.199 mmol) were mixed in DCM (3 ml). PS-DIEA (3.66 mmol/g, 272 mg, 0.997 mmol) was added. The mixture was shaken at room temperature over a weekend. It was then loaded on a column (ISOLUTE® S... | COC(=O)c1ccccc1COc1ccc(CCNS(=O)(=O)Cc2ccccc2)cc1 | null | 19.4 | null |
839,011 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=3[N:16]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(=O)([O-])[O-].[K+].[K+].Cl[C:39]1[CH:44]=[CH:43][N:42]=[C:41]([NH:45][C:46]([CH:48]2[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:4... | CC(C)(C)c1cccc(Nc2nc3cc(O)ccc3s2)c1 | CN1CCC(C(=O)Nc2cc(Cl)ccn2)CC1 | null | C[Si](C)(C)[N-][Si](C)(C)C | O=C([O-])[O-] | [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 | 25 | 0.17 | The mixture containing 2-(3-tert-butylphenylamino)benzo[d]thiazol-5-ol (1 eq), potassium bis(trimethylsilyl)amide (4 eq), and potassium carbonate (1.2 eq) in dimethylformamide was stirred at room temperature for 10 minutes. N-(4-chloropyridin-2-yl)-1-methylpiperidine-4-carboxamide (1.4 eq) was then added and mixture su... | CN1CCC(C(=O)Nc2cc(Oc3ccc4sc(Nc5cccc(C(C)(C)C)c5)nc4c3)ccn2)CC1 | null | null | null |
1,508,645 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:23]=[CH:22][C:15]([CH2:16]OS(C)(=O)=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([CH3:27])([CH3:26])[CH3:25].C(=O)(O)[O-].[K+]>CN(C=O)C>[C:24]([O:28][C:29](=[O:37])[NH:30][CH... | CS(=O)(=O)OCc1ccc(NC(=O)OCc2ccccc2)cc1 | CC(C)(C)OC(=O)NC1CCNCC1 | 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 | 60 | 16 | Methanesulfonic acid 4-benzyloxycarbonylamino-benzyl ester (0.35 g, 2.5 mmol) was added to a suspension of piperidin-4-yl-carbamic acid tert-butyl ester (0.15 g, 0.76 mmol) and potassium bicarbonate (0.35 g, 2.5 mmol) in DMF (10 ml) and the reaction heated to 60° C. and stirred at this temperature for 16 hours under a ... | CC(C)(C)OC(=O)NC1CCN(Cc2ccc(NC(=O)OCc3ccccc3)cc2)CC1 | null | 41.9 | null |
1,392,599 | ord_dataset-12dc3bd21bcf44d09e5b4249afe15161 | null | 2014-01-01T00:02:00 | true | [C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC(CO[C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2[CH:26]=[O:27])=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:25][N:24]1[C:20]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[C:21]([CH:26]=[O:27])[CH:... | Cn1ncc(C=O)c1OCc1ccc(Cl)cc1 | c1ccc(N2CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | CN(C)C=O | null | null | null | null | null | null | null | null | null | 120 | 8 | A mixture of 1-phenylpiperazine (3.40 g), 5-[(4-chlorobenzyl)oxy]-1-methyl-1H-pyrazol-4-carbaldehyde (600 mg), triethylamine (1.20 mL) and dimethylformamide (7.0 mL) was stirred at 120° C. for 8 hours, and then at a room temperature for 17 hours. Thereafter, the reaction solution was concentrated under a reduced pressu... | Cn1ncc(C=O)c1N1CCN(c2ccccc2)CC1 | null | 103.4 | null |
864,858 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | O[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.FC(F)(F)C(O)=O>>[C:14]1([C:2]2[CH2:3][NH:4][CH2:5][CH:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1 | CC(C)(C)OC(=O)N1CCC(O)(c2ccccc2)C1 | 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 | 25 | 1 | A mixture of tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate (0.36 g, 0.0014 mol) and trifluoroacetic acid (2.0 mL, 0.026 mol) was stirred under nitrogen at room temp for 1 h. The volatile was removed under vacuum and evaporated with toluene twice. The residue was used in next step w/o further purification. LCMS... | C1=C(c2ccccc2)CNC1 | null | null | null |
967,533 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [NH2:1][C@H:2]([CH2:20][C:21]1[N:22]=[CH:23][N:24](CC2C=CC=CC=2)[CH:25]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])=[C:8]([CH3:19])[CH:7]=1)=[O:4].[H][H]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH2:1][C@H:2]([CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[C:3]([NH:5][C:6]1[CH:... | Cc1cc(NC(=O)[C@H](N)Cc2cn(Cc3ccccc3)cn2)ccc1C(=O)N1CCCC1 | [H][H] | null | [Pd+2] | [OH-] | 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 | null | null | 350.0 mg (0.81 mmol) (R)-2-amino-3-(1-benzyl-1H-imidazol-4-yl)-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-propionamide are dissolved in 10.0 ml acetic acid and combined with 150.0 mg Pd(OH)2. The mixture is hydrogenated in a Parr apparatus at ambient temperature at 3 bar hydrogen pressure for eight hours. Then th... | Cc1cc(NC(=O)[C@H](N)Cc2c[nH]cn2)ccc1C(=O)N1CCCC1 | null | null | null |
1,352,683 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | N#N.[CH2:3]1[CH2:13][CH2:12][N:11]2[C:6](=NCC[CH2:10]2)[CH2:5][CH2:4]1.BrCCCC#[N:19]>CCOCC>[N:11]1([CH2:12][CH2:13][CH2:3][CH2:4][NH2:19])[CH2:10][CH2:5][CH2:6]1 | C1CCC2=NCCCN2CC1 | N#CCCCBr | null | N#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | null | In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of trimethylene imine (300 mg, 5.25 mmol) and DBU (0.79 mL, 5.23 mmol) in dry Et2O (4 mL) was added 4-bromobutyronitrile (0.54 mL, 5.27 mmol) at 0° C. The reaction mixture was stirred at rt until compl... | NCCCCN1CCC1 | null | null | null |
66,462 | ord_dataset-8af141577c90485cb9c91079a5ef96b3 | null | 1980-01-01T00:05:00 | true | [F:1][C:2]([F:29])([F:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.B(F)(F)F.CCOCC.[CH:39](O)([CH3:41])[CH3:40]>>[F:1][C:2]([F:28])([F:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:... | CC(C)O | O=C(O)c1ccc(NCCCCCCCCCCCCCCCC(F)(F)F)cc1 | null | FB(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 0 | null | A solution of 50.5 g of 4-[15-(trifluoromethyl)pentadecylamino]benzoic acid and 34.4 ml. of boron trifluoride etherate in 200 ml. of isopropyl alcohol is stirred under reflux for 44 hours, allowed to cool, and poured into 1.20 liters of ice cold 5% aqueous sodium carbonate solution. The white solid is collected by filt... | CC(C)OC(=O)c1ccc(NCCCCCCCCCCCCCCCC(F)(F)F)cc1 | null | null | null |
1,272,815 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [C:1]([CH2:4][C:5]1[CH:41]=[CH:40][C:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=2[C@@H:23]2[CH2:32][CH2:31][C:30]3[CH:29]=[C:28]([O:33]C(=O)C(C)(C)C)[CH:27]=[CH:26][C:25]=3[CH2:24]2)=[CH:7][CH:6]=1)(O)=O.[CH2:42]([NH:46][CH3:47])[CH2:43][CH2:44][CH3:45]>>[... | CCCCNC | COc1cc(NCCCc2ccc(CC(=O)O)cc2)c([C@@H]2CCc3cc(OC(=O)C(C)(C)C)ccc3C2)cc1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesized from pivalic acid (R)-6-{2-[(4-carboxymethylbenzyl)ethylamino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (19 mg) and butylmethylamine (22 mg) according to an analogous synthetic method to Example 715 and purified by LC-MS, the title compound (3.4 mg) was obtained. | CCCCN(C)CCc1ccc(CCCNc2cc(OC)c(OC)cc2[C@@H]2CCc3cc(O)ccc3C2)cc1 | null | 18.9 | null |
370,547 | ord_dataset-15cdba4c7f064b3f9cd7343cb3187881 | null | 1997-01-01T00:07:00 | true | CC(C)([O-])C.[K+].[CH2:7]([S:9][C:10]1[NH:11][C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]([C:15]([OH:18])([CH3:17])[CH3:16])[N:14]=1)[CH3:8].[C:24]([N:43]1[C:47]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=2[C:54]2[CH:61]=[CH:60][C:57]([CH2:58]Br)=[CH:56][CH:55]=2)=[N:46][N:45]=[N:44]1)([C:37]1[CH:42]=[CH:41][C... | BrCc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)c1[nH]c(SCC)nc1C(C)(C)O | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | null | 0.5 | 478 mg of potassium t-butoxide were added to a solution of 1.00 g of ethyl 2-ethylthio-4-[1-hydroxy-1-methylethyl)imidazole-5-carboxylate [prepared as described in Preparation 50(ii)] in 20 ml of N,N-dimethylacetamide, whilst ice-cooling, and the mixture was stirred for 30 minutes. At the end of this time, 2.59 g of 4-... | CCOC(=O)c1c(C(C)(C)O)nc(SCC)n1Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | 78 | null |
492,443 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [C:1]1(=[N:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26](OCC)=O)[CH2:19][CH2:18]2)=[C:13]([CH3:31])[CH:12]=1>>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]3[O:9][N... | CCOC(=O)CCCN1CCC(c2ccc(Cl)cc2C)CC1 | ON=C1CCCCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | By the same reaction and treatment as in Example 48 using cycloheptanone oxime and ethyl 4-(4-(4-chloro-2-methylphenyl)piperidin-1-yl)-n-butyrate, 3-(3-(4-(4-chloro-2-methylphenyl)piperidin-1-yl)propyl)-5,6,7,8-tetrahydro-4H-cyclohepta[c]isoxazole is obtained. | Cc1cc(Cl)ccc1C1CCN(CCCc2onc3c2CCCCC3)CC1 | null | null | null |
1,270,790 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)=[C:12]([CH:18]=2)[C:13]([O:15]CC)=[O:14])[CH:5]=[N:6][CH:7]=1.[OH-].[Li+].Cl>C(O)(C)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)=[C:12]([CH:18]=2)[C:13]([OH:15])=[... | CCOC(=O)c1cc(-c2cncc(C)c2)ccc1-c1cnccn1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)O | null | null | null | null | null | null | null | null | null | 60 | null | To a mixture of ethyl 5-(5-methylpyridin-3-yl)-2-pyrazin-2-ylbenzoate (3-3, 0.065 g, 0.204 mmol, 1.0 equiv) in isopropanol/water (3:1, 2 mL) was added 1M lithium hydroxide solution (0.244 mL, 0.244 mmol, 1.2 equiv) and the reaction was heated to 60° C. for 30 minutes in the microwave. The reaction mixture was cooled an... | Cc1cncc(-c2ccc(-c3cnccn3)c(C(=O)O)c2)c1 | null | null | null |
423,133 | ord_dataset-1a231de00bfe4443b547e1f03885ed41 | null | 1999-01-01T00:01:00 | true | [OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[C:3]=1[CH:21]=[O:22].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](... | C[C@]12CC[C@@H]3c4ccc(O)c(C=O)c4CC[C@H]3[C@@H]1CC[C@@H]2O | null | null | O=[Cr](=O)=O | O=S(=O)(O)O | 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 | null | 0.17 | To a solution of 3,17β-dihydroxyestra-1,3,5(10)-triene-4-carboxaldehyde (2b, 0.300 g, 1.0 mmol) in acetone (10 mL) was added Jones reagent (0.50 mL) at 0° C. The reaction mixture was stirred for 10 min, quenched with 2-propanol, and extracted with EtOAc. The combined organic layers were washed with H2O, then with satur... | C[C@]12CC[C@@H]3c4ccc(O)c(C=O)c4CC[C@H]3[C@@H]1CCC2=O | null | 92.5 | null |
794,707 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl.[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14]Cl)[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:10]([N:12]([CH2:16][CH3:17])[CH2:13][CH2:14][S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[CH3:11] | CCN(CC)CCCl | Nc1ccc(S)cc1 | null | Cl | 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 | 60 | null | To a solution of 4-aminothiophenol (23.0 mmol, 2.88 g) in DMF (23 mL) was added 2-(diethylamino)ethyl chloride hydrochloride (11.5 mmol, 1.98 g) and cesium carbonate (34.5 mmol, 11.2 g). The resulting mixture was heated to 60° C. for 3 hours. The solvent was removed by rotary evaporation. The residue was partitioned be... | CCN(CC)CCSc1ccc(N)cc1 | null | 48.8 | null |
965,452 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[Mg]Br.C1COCC1>>[C:10]([O:9][C:8](=[O:14])[NH:7][C@@H:5]([CH3:6])[C:4]([C:19]1[CH:18]=[CH:17][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:2... | CON(C)C(=O)[C@H](C)NC(=O)OC(C)(C)C | Br[Mg]c1ccc2ccccc2c1 | 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 | null | null | The subtitle compound was prepared analogous to the method described in Example 19 (step 19d), starting from (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (1.86 g, 8 mmol) and a freshly prepared 2-Naphthylmagnesiumbromide 1M solution in THF (8 mL, 8 mmol). The obtained material was crystallised from... | C[C@H](NC(=O)OC(C)(C)C)C(=O)c1ccc2ccccc2c1 | null | null | null |
1,038,077 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][CH:15]([O:18][Si... | COc1cc([N+](=O)[O-])ccc1N1CCC(O[Si](C(C)C)(C(C)C)C(C)C)CC1 | null | null | [Pd] | 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 | 25 | 3 | Dissolve 1-(2-Methoxy-4-nitro-phenyl)-4-triisopropylsilanyloxy-piperidine (1.53 g, 3.74 mmol) in THF (30 mL) and add 5% Pd/C then stir the slurry at room temperature under a hydrogen atmosphere for 3 h. Filter the black mixture through a pad of Celite® and concentrate the filtrate in vacuo to give 3-methoxy-4-(4-triiso... | COc1cc(N)ccc1N1CCC(O[Si](C(C)C)(C(C)C)C(C)C)CC1 | null | 100.3 | null |
658,660 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | ClC[CH2:3][S:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2C(C3C=CC(O)=CC=3)=C(C(F)(F)F)C3C=CC(O)=CC=3[O:12]2)=[CH:7][CH:6]=1.[I-].[K+].O.C(OCC)(=[O:38])C>N1CCCCC1>[CH3:3][S:4]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][CH:6]=1)=[O:38] | CCOC(C)=O | Oc1ccc(C2=C(C(F)(F)F)c3ccc(O)cc3OC2c2ccc(SCCCl)cc2)cc1 | null | [I-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCNCC1 | null | null | null | null | null | null | null | null | null | 100 | 6 | 220 mg of 2-[4-(3-chloro-1-thiapropyl)-phenyl]-7-hydroxy-3-(4-hydroxyphenyl)-4-(trifluoromethyl)-2H-1-benzopyran in 2 ml of piperidine is mixed with 42.7 mg of potassium iodide and stirred for 6 hours at 100° C. After cooling, it is poured into water and shaken out three times with ethyl acetate. The combined organic p... | CS(=O)c1ccc(C=O)cc1 | null | null | null |
859,820 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [NH2:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[CH:6]=[N:5]1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C1COCC1>[CH2:24]([O:23][C:21](=[O:22])[NH:1][C@@H:2]([CH3:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[C... | O=C(Cl)OCc1ccccc1 | C[C@H](N)Cn1ncc2ccc(O)cc21 | null | O=C([O-])O | [Na+] | 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 | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol [prepared in accordance with commonly owned WO 02/098862A1, the contents of which are by this reference incorporated herein] (2.00 g, 10.5 mmol) was suspended in THF (20 mL) and saturated aqueous sodium bicarbonate (10 mL) and benzyl chloroformate (1.50 mL, 15 mol) were added. The ... | C[C@@H](Cn1ncc2ccc(O)cc21)NC(=O)OCc1ccccc1 | null | 78 | null |
1,129,206 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+:35].O>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:... | CCOC(=O)CCn1ccc2c(-c3noc(-c4ccc(OC(C)C)c(C#N)c4)n3)cccc21 | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | 50 | 0.5 | Ethyl 3-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate (D63) (81 mg, 0.18 mmol) was dissolved in ethanol by warming to 50° C. Added 2N sodium hydroxide (0.25 ml, 0.5 mmol) followed by water (2 ml), warmed to 50° C. to give a clear solution then left standing at RT for 30 min... | CC(C)Oc1ccc(-c2nc(-c3cccc4c3ccn4CCC(=O)[O-])no2)cc1C#N | null | null | null |
436,416 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | [CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[C:10]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:4].[H-].[Na+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C)C=O>[CH2:35]([O:34][C:32]([CH2:31][N:12]1[C:13]2[C:18](=[C... | COC(=O)C1=C(c2c(-c3ccccc3)[nH]c3cc(C(=O)O)ccc23)CCC1 | CCOC(=O)CBr | null | [H-] | [Na+] | 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 | 25 | 0.5 | To a suspension of 3-(2-methoxycarbonyl-cyclopent-1-enyl)-2-phenyl-1H-indole-6-carboxylic acid on Wang resin (100 mg; compound 7-3, prepared according to the is procedure outlined in Example 7) in dimethylformamide (1.5 mL) was added sodium hydride (60% in mineral oil; 20 mg) and the mixture was stirred at room tempera... | CCOC(=O)Cn1c(-c2ccccc2)c(C2=C(C(=O)OC)CCC2)c2ccc(C(=O)O)cc21 | null | null | null |
639,160 | ord_dataset-1c0bae7388cf460091d56129e95b3145 | null | 2004-01-01T00:06:00 | true | [OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[CH:13]=[CH2:12] | COc1ccc(C=O)c(O)c1 | C=CCBr | null | O=C([O-])[O-] | [K+] | 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 | null | null | To a solution of 100 g of 2-hydroxy-4-methoxybenzaldehyde in 2 liters of acetone add 79.5 ml of allyl bromide and then, gradually, 272 g of potassium carbonate. Heat at reflux for 4 hours and then filter; concentrate the filtrate in vacuo, take up the residue in 1 liter of dichloromethane and wash the solution with 1N ... | C=CCOc1cc(OC)ccc1C=O | null | null | null |
366,709 | ord_dataset-b18df02d6e9345faa0f2dae281a0870a | null | 1997-01-01T00:06:00 | true | [C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[O:8]=[C:9]([CH3:21])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](CCO)=[CH:14][CH:13]=1.O1CCCC1>N1C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9](=[O:8])[CH3:21])=[CH:13][CH:14]=1)(=[O:7])[CH3:6] | CC(=O)OC(C)=O | CC(=O)COc1ccc(CCO)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 3.5 | 1.96 g of acetic anhydride were added, whilst ice-cooling, to a mixture of 3.1 g of 2-[4-(2-oxopropoxy)phenyl]ethanol (prepared as described in Preparation 7), 50 ml of anhydrous tetrahydrofuran and 2.53 g of pyridine, and the resulting mixture was stirred at room temperature for 3.5 hours. At the end of this time, 12.... | CC(=O)COc1ccc(CCOC(C)=O)cc1 | null | null | null |
685,654 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[NH:21][C:22](=[O:39])[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[CH:33]=2)[CH:27]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:16][N:14]([CH3:15])[C:12]1[C:... | Cc1cc(-c2cccc(C(=O)CC(=O)Nc3cc(C(F)(F)F)c(N(C)C)cc3NC(=O)OC(C)(C)C)c2)ccn1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from (5-dimethylamino-2-{3-[3-(2-methyl-pyridin-4-yl)-phenyl]-3-oxo-propionylamino}-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example M71) (0.45 g, 0.81 mmol) by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a light yellow solid (205 mg, 5... | Cc1cc(-c2cccc(C3=Nc4cc(N(C)C)c(C(F)(F)F)cc4NC(=O)C3)c2)ccn1 | null | null | null |
1,503,055 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | CS(O)(=O)=O.[NH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH:18]1[CH2:23][CH2:22][C:21](=[O:24])[NH:20][C:19]1=[O:25])[CH2:11]2.[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:34]=[CH:33][C:32]([N:35]=[C:36]=[O:37])=[CH:31][CH:30]=1.C(N(CC)CC)C.Cl>CN(C)C=O>[O:25]=[C:19]1[CH:18]([N:12]2[... | NCc1ccc2c(c1)CN(C1CCC(=O)NC1=O)C2=O | O=C=Nc1ccc(OC(F)(F)F)cc1 | null | CS(=O)(=O)O | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | 2 | To a stirred mixture of 3-(5-aminomethyl-1-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione methane sulfonate (0.50 g, 1.40 mmol) and 4-(trifluoromethoxy)phenylisocyanate (0.20 mL, 1.40 mmol) in N,N-dimethylformamide (10 mL), was added triethylamine (0.38 mL, 2.7 mmol) at room temperature under nitrogen. After 2 h, ... | O=C1CCC(N2Cc3cc(CNC(=O)Nc4ccc(OC(F)(F)F)cc4)ccc3C2=O)C(=O)N1 | null | 64.5 | null |
1,592,321 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][C:2]1[NH:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:7](=[O:14])[C:6]=12.C(N=C=NCCCN(C)C)C.O/[N:40]=[C:41](\[NH2:48])/[C:42]1[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=1>CN(C)C=O.N1C=CC=CC=1>[CH3:1][C:2]1[NH:... | N/C(=N\O)c1cccnc1 | Cc1[nH]c(-c2ccccc2Oc2ccccc2)c2cc(C(=O)O)[nH]c(=O)c12 | null | CCN=C=NCCCN(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | c1ccncc1 | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of Example 12b (200 μL, 0.0275 g, 0.076 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (200 μL, 0.0225 g, 0.145 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), and a solution of (Z)—N′-hydroxynicotinimidamide (173.0 μL, 0.103 mmol) in 1 mL of... | Cc1[nH]c(-c2ccccc2Oc2ccccc2)c2cc(-c3nc(-c4cccnc4)no3)[nH]c(=O)c12 | null | 8.8 | null |
1,127,826 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]#[N:12])[C:3]=1[Cl:13].[OH-].[Na+].Cl>CO>[Cl:13][C:3]1[C:4]([C:11]#[N:12])=[C:5]([CH:9]=[CH:10][CH:2]=1)[C:6]([OH:8])=[O:7] | Cc1ccc(C(=O)O)c(C#N)c1Cl | null | null | Cl | [Na+] | [OH-] | 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 | The mixture of 430 mg of methyl 3-chloro-2-cyanobenzoic acid obtained by the same manner as in U.S. Pat. No. 4,900,739, 22 ml of methanol and 2.5 ml of aqueous sodium hydroxide (1 mol/l) was stirring at room temperature for 2 hours. To the reaction mixture was added hydrochloride (5 mol/l) and was extracted with chloro... | N#Cc1c(Cl)cccc1C(=O)O | null | null | null |
871,800 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Mg].II.[CH3:13][C:14]([CH3:34])([CH3:33])[CH2:15][C:16]([NH:18][C:19]1[C:20]([CH3:32])=[C:21]([CH3:31])[C:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24](=[O:29])[C:23]=2[CH:30]=1)=[O:17]>C1COCC1>[OH:29][C:24]1([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[... | ClCCc1ccccc1 | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2=O | null | II | [Mg] | 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 | 25 | 1 | A solution of 2-chloroethylbenzene (648 mg, 4.6 mmol) in THF (5 mL) was added dropwise under an argon atmosphere to a mixture of magnesium (112 mg, 4.6 mmol) and a catalytic amount of iodine, and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise a solution of 3,3-dimethyl-N-(2,2,6,7-te... | Cc1c(NC(=O)CC(C)(C)C)cc2c(c1C)OC(C)(C)C2(O)CCc1ccccc1 | null | 50.1 | null |
1,709,378 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9](=O)[C:10]([F:13])([F:12])[F:11].[Cl:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](Cl)=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:22](=[O:23])[C:21]([O:20][C:19]1[CH:25]=[CH:26][C:16]([Cl:15])=[CH:17... | Nc1ccc(Br)cc1C(=O)C(F)(F)F | O=C(Cl)COc1ccc(Cl)cc1 | 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 | 0 | 2 | To a solution of 1-(2-amino-5-bromophenyl)-2,2,2-trifluoroethanone (2.76 g, 10.3 mmol, Intermediate 7, step b) in dichloromethane (20 mL) was added commercially available 2-(4-chlorophenoxy)acetyl chloride (2.11 g, 10.3 mmol). The resulting white solution was cooled with an ice bath to 0° C. and treated with triethylam... | O=c1[nH]c2ccc(Br)cc2c(C(F)(F)F)c1Oc1ccc(Cl)cc1 | null | null | null |
306,823 | ord_dataset-a6643d22de674f30a85ba57198b82644 | null | 1995-01-01T00:03:00 | true | [CH2:1]([O:8][C:9]([C@@H:11]([N:27]([C:65](=[O:70])[CH2:66][CH2:67][CH2:68][CH3:69])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[N:45](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:44]=[N:43][N:42]=2)=[CH:31][CH:30]=1)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][... | CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnnn2C(c2ccccc2)(c2ccccc2)c2ccccc2)cc1)[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | null | Cl | 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 | 4.5 | 1.07 g of (S)-N-(1-benzyloxycarbonyl-5-benzyloxycarbonylamino-pent-1-yl)-N-pentanoyl-N-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine are dissolved in 15 ml of dioxane. This solution is treated with 1.5 ml of a solution of hydrogen chloride in dioxane (7 N), the mixture is stirred for 4.5 hours at 4... | CCCCC(=O)N(Cc1ccc(-c2ccccc2-c2nnn[nH]2)cc1)[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)OCc1ccccc1 | null | null | null |
893,876 | ord_dataset-11068b1e475b4c5b82e56726ab0dddb7 | null | 2009-01-01T00:07:00 | true | [C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:30]=3[N:29]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:39](O)[CH2:40][CH... | CCCCOC(=O)c1ccc2c(c1)CCC2N(c1nc2cc(O)ccc2n1C)[C@H]1CC[C@H](C(C)(C)C)CC1 | CCCO | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 25 | 2 | To a solution of butyl 1-[(trans-4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1H-benzimidazol-2-yl)amino]indane-5-carboxylate (49.0 mg, 0.095 mmol) in dry dichloromethane was added 1-propanol (18.0 □L, 0.24 mmol), diisopropyl azodicarboxylate (37.0 μL, 0.19 mmol) and Ph3P (50.0 mg, 0.19 mmol). After stirring at room temp... | CCCCOC(=O)c1ccc2c(c1)CCC2N(c1nc2cc(OCCC)ccc2n1C)[C@H]1CC[C@H](C(C)(C)C)CC1 | null | null | null |
330,971 | ord_dataset-1558660634294cc8ad7e01746e9083fd | null | 1996-01-01T00:06:00 | true | [N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8]=2[CH:17]=1)([O-])=O>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:8]=2[CH:17]=1 | COC(=O)Cc1nsc2ccc([N+](=O)[O-])cc12 | 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 | 50 | null | Iron (0.74 g, 13.3 mmol) is added portionwise to a solution of methyl 5-nitro-1,2-benzisothiazole-3-acetate (0.67 g, 2.7 mmol) in acetic acid at 50° C. The reaction mixture is stirred at 50° C. for several minutes, cooled and filtered through diatomaceous earth. The resultant filtrate, which contains the title product,... | COC(=O)Cc1nsc2ccc(N)cc12 | null | null | null |
164,100 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]=[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)[C:14]=1[C:34](OC)=[O:35]>O1CCCC1>[OH:35][CH2:34][C:14]1[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[... | COC(=O)c1c(C)nc(-c2ccccc2)nc1-c1cccc([N+](=O)[O-])c1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCOCC | null | null | null | null | null | null | null | null | null | 0 | null | To a suspension of lithium aluminum hydride (12.24 g) in a mixture of dry tetrahydrofuran (180 ml) and diethyl ether (360 ml) was dropwise added a solution of methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylate in dry tetrahydrofuran (180 ml) under cooling at -50°~-40° C. The excess lithium aluminum hydr... | Cc1nc(-c2ccccc2)nc(-c2cccc([N+](=O)[O-])c2)c1CO | null | null | null |
433,044 | ord_dataset-386da077ab2340638cada986e2ef0770 | null | 1999-01-01T00:07:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=S)[NH:7][C:6]=2[CH:17]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1>C(OCCO)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH... | S=C1Nc2cc(Cl)ccc2Nc2ccccc21 | NCc1cccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCCO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.39 g (1.5 mmol) of 8-chloro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-thione (Hunziker F., et al., Helv. Chim. Acta, 50:1588 (1967)) in 10 mL of 2-ethoxyethanol was treated with 0.3 mL (2.99 mmol) of 3-(aminomethyl)pyridine and heated at reflux for 30 hours. The solvent was removed under reduced pressur... | Clc1ccc2c(c1)N=C(NCc1cccnc1)c1ccccc1N2 | null | 39.8 | null |
590,586 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH:7]=O.Cl.[NH2:10][OH:11].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH:7]=[N:10][OH:11] | NO | Cc1ncoc1C=O | null | Cl | O=C([O-])[O-] | [K+] | 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 | 2 | 0.50 g (4.50 mmol) of 4-methyl-1,3-oxazole-5-carbaldehyde [prepared from the corresponding alcohol (Chem. Ber. 1961, 1248) by Swern oxidation (Tetrahedron 34, 1651 (1978))] is initially charged in 3 ml of water and treated with 0.66 g (9.45 mmol) of hydroxylamine hydrochloride in 2 ml of water. 0.68 g (4.95 mmol) of po... | Cc1ncoc1C=NO | null | null | null |
1,624,979 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O1[CH2:22][CH2:21][NH:20]C1=O>>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[O:15][CH2:22][CH2:21][NH2:20])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1 | O=C1NCCO1 | O=C1c2ccccc2Cc2ccccc21 | null | [K+] | [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 | null | 25 | 2.5 | ExxonMobil™ Aromatic 100 solvent vvas added into a 3-neck round bottom flask containing anthrone (10 g, 51.5 mmol) at room temperature. Potassium hydroxide pellets (0.33 g, 5.15 mmol) and 2-oxazolidinone (7.62 g, 87.5 mmol) were added, and the reaction mixture was heated to reflux and stirred for 2.5 h under nitrogen. ... | NCCOc1c2ccccc2cc2ccccc12 | null | 35.2 | null |
1,534,648 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [H-].[Na+].[F:3][C:4]1[C:9]([C:10]2[NH:14][CH:13]=[C:12]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=2[F:25])=[CH:8][CH:7]=[CH:6][N:5]=1.C1OCCOCCOCCOCCOC1.[O:41]1[CH:45]=[CH:44][CH:43]=[C:42]1[S:46](Cl)(=[O:48])=[O:47]>O1CCCC1.O>[F:25][C:11]1[C:12]([CH2:15][N:16]([CH3:24])[C:1... | CN(Cc1c[nH]c(-c2cccnc2F)c1F)C(=O)OC(C)(C)C | O=S(=O)(Cl)c1ccco1 | null | C1COCCOCCOCCOCCO1 | [H-] | [Na+] | 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 | 1 | To a suspension of sodium hydride (60% in oil, 37 mg) in tetrahydrofuran (2 mL) were added dropwise a solution of tert-butyl {[5-(2-fluoropyridin-3-yl)-4-fluoro-1H-pyrrol-3-yl]methyl}methylcarbamate (200 mg) in tetrahydrofuran (1 mL), 15-crown-5 (205 mg) and 2-furansulfonyl chloride (132 mg) under ice-cooling and the m... | CN(Cc1cn(S(=O)(=O)c2ccco2)c(-c2cccnc2F)c1F)C(=O)OC(C)(C)C | null | 86.6 | null |
360,337 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][Si](C)(C)C)=[CH:9][CH:10]=2)[N:5]([CH:18]([CH3:20])[CH3:19])[C:4](=[O:21])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:22][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([CH:18]([CH3:19])[CH3:20])[C:4](=[O:21])[CH2:3]1 | CC(C)N1C(=O)CC(C)(C)c2ccc(C#C[Si](C)(C)C)cc21 | null | null | O=C([O-])[O-] | [K+] | 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 | 25 | 10 | To a solution of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-isopropyl-7-[(trimethylsilyl)ethynyl]quinoline (Compound 29) in 7.0 ml of methanol was added potassium carbonate. The mixture was stirred at room temperature for 10 h. The reaction mixture was then concentrated in vacuo and the resulting oil was dissolved in wate... | C#Cc1ccc2c(c1)N(C(C)C)C(=O)CC2(C)C | null | null | null |
863,417 | ord_dataset-b8b98725045d45bdbd73512048f4b47e | null | 2009-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:4]=1[CH2:5][N:6]([CH2:27][CH2:28][CH2:29][CH3:30])[C:7](=[O:26])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C@H:17]([O:23][CH2:24][CH3:25])[C:18]([O:20]CC)=[O:19])=[CH:12][CH:11]=1.[Li+].[OH-].Cl>C(#N)C>[CH2:27]([N:6]([CH2:5][C:4]1[CH:31]=[CH:32][C... | CCCCN(Cc1cccc(OC)c1OC)C(=O)COc1ccc(C[C@H](OCC)C(=O)OCC)cc1 | null | null | Cl | [Li+] | [OH-] | 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 | 25 | 8 | To a solution of ethyl(2S)-3-(4-{2-[(2,3-dimethoxybenzyl)(butyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate (1.02 g, 2.0 mmol) in acetonitrile (80 mL) was added aqueous 0.10 M LiOH (40 mL) and the reaction mixture was stirred at room temperature overnight. The solvent volume was reduced in vacuo and the remaining aqu... | CCCCN(Cc1cccc(OC)c1OC)C(=O)COc1ccc(C[C@H](OCC)C(=O)O)cc1 | null | 101.4 | null |
47,293 | ord_dataset-6d529f04a1724b5d85dcc290cf4c38bb | null | 1978-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>>[C:9]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)(=[O:11])[CH3:10] | Nc1cccc(Br)n1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 20 g (0.116 mole) of 2-amino-6-bromopyridine was dissolved in 140 ml. acetic anhydride and heated at 70° C for 45 minutes. 2-Acetamido-6-bromopyridine was isolated by filtration as white flakes, m.p.=159.2°-160.0° C, in 68% yield. The excess acetic anhydride present in the reaction mixture was hydrolyzed by the additio... | CC(=O)Nc1cccc(Br)n1 | null | 68 | null |
142,556 | ord_dataset-84dc0c9e5fb4424687194ef8d14d1c22 | null | 1986-01-01T00:04:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.[F:14][B-:15]([F:18])([F:17])[F:16].[H+].[N:20](OCCCCC)=O>C(O)C.C(OCC)C>[F:14][B-:15]([F:18])([F:17])[F:16].[N+:1](=[C:2]1[CH:7]=[N:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[C:4]([CH3:13])[CH2:3]1)=[N-:20] | CCCCCON=O | Cc1cc(N)cnc1CCCCN | null | F[B-](F)(F)F | [H+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.25 | A cooled (0° C.) mixture of 5-amino-2-[4-amino-butyl]-3-methylpyridine (0.86 g) and fluoroboric acid (5 ml) in ethanol (30 ml) was reacted with amyl nitrite (3 ml) over 15 minutes and then stirred for a further 15 minutes, diluted with diethyl ether at 0° C. to give 5-diazo-2-(4-aminobutyl)-3-methylpyridine fluoroborat... | CC1=C(CCCCN)N=CC(=[N+]=[N-])C1 | null | null | null |
803,136 | ord_dataset-ed846b4b229e4bb09ad9dba95ad7ebeb | null | 2008-01-01T00:01:00 | true | [C:1]([CH:4]([C:15](=[O:17])[CH3:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[Cl-].[Mg+2].[Cl-].N1C=CC=CC=1.[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)#[N:28]>ClCCl>[C:1]([C:4]([C:33](=[O:34])[C:32]1[CH:36]=[CH:37][C:29]([C:27]#[N:28])=[CH:30... | N#Cc1ccc(C(=O)Cl)cc1 | CCOC(=O)CCCCCC(C(C)=O)C(C)=O | null | [Cl-] | [Mg+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 20 | 1 | To a mixture of ethyl 7-acetyl-8-oxononanoate (4.0 g) and magnesium chloride (1.27 g) in dichloromethane (70 ml) was added pyridine (2.15 ml) at 0° C. The mixture was stirred at 20° C. for 1 hour, then a solution of 4-cyanobenzoyl chloride (2.87 g) in dichloromethane (10 ml) was added. After stirring for 3 hours at 20°... | CCOC(=O)CCCCCC(C(C)=O)(C(C)=O)C(=O)c1ccc(C#N)cc1 | null | 5,740.9 | null |
1,389,741 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | OS(C(F)(F)F)(=O)=O.[C:9](=[NH:32])([O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)=[CH:16][CH:15]=1)[NH2:10].[C:33]([C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH:42]([CH:48]=O)[C:43](OCC)=[O:44])=[CH:37][CH:36]=1)#[N:34].C([O-])([O... | CCOC(=O)C(C=O)Cc1ccc(C#N)cc1 | N=C(N)OCCc1ccc(Oc2ccc(Cl)c(C(F)(F)F)c2)cc1 | null | O=C([O-])[O-] | O=S(=O)(O)C(F)(F)F | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | null | 160 | null | The mixture of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate triflate (120 mg, 0.236 mmol), ethyl 3-(4-cyanophenyl)-2-formylpropanoate (137 mg, 0.591 mmol) and K2CO3 (98 mg, 0.709 mmol) in DMA (5 mL) was heated with a microwave reactor at 160° C. for 1 hour. Purification via MDAP then afford... | N#Cc1ccc(Cc2c[nH]c(OCCc3ccc(Oc4ccc(Cl)c(C(F)(F)F)c4)cc3)nc2=O)cc1 | null | 30.6 | null |
44,790 | ord_dataset-ff0bcb6c2300494cbdf16005ad32ad5f | null | 1978-01-01T00:08:00 | true | [C:1]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11](Cl)[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH3:20][OH:21]>O>[C:1]([C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[C:11]([O:21][CH3:20])[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | O=C(c1ccccc1)c1nc(Cl)ccc1[N+](=O)[O-] | CO | 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 | null | null | 60 grams of 2-benzoyl-3-nitro-6-chloropyridine were added in portions to a solution of 10 grams of sodium metal in 500 ml. of methanol at 50° C. with stirring, whereby the temperature gradually increased. Then the mixture was heated under reflux for four hours and subsequently treated with two liters of water. The prec... | COc1ccc([N+](=O)[O-])c(C(=O)c2ccccc2)n1 | null | null | null |
1,770,835 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [N+:1]([CH:4]1[CH2:9][N:8]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:12]([C:13]#[N:14])=[C:7]2[NH:6][CH2:5]1)([O-])=O>CO.C(Cl)Cl.[Pd]>[NH2:1][CH:4]1[CH2:9][N:8]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:2... | N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn2c1NCC([N+](=O)[O-])C2 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CO | null | null | null | null | null | null | null | null | null | 25 | 2 | To a solution of 6-nitro-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (600 mg, 1.67 mmol) in 30 mL of methanol and 10 mL of DCM was added 10% w/w Pd/C (100 mg). The mixture was stirred at RT under H2 for 2 hr and filtered. The filtrate was concentrated and purified by chromatography co... | N#Cc1c(-c2ccc(Oc3ccccc3)cc2)nn2c1NCC(N)C2 | null | 36.1 | null |
1,338,657 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([C:16]([F:19])([F:18])[F:17])=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:4][C:3]=1[O:20][CH3:21].[N+:22]([O-])([OH:24])=[O:23]>C(O)(=O)C>[OH:1][C:2]1[C:7]([N+:22]([O-:24])=[O:23])=[CH:6][C:5]([C:8]([C:10]2[C:11]([C:16]([F:17])([F:18])[F:19])=[N:12][CH:13]=[CH:14][CH:15... | O=[N+]([O-])O | COc1cc(C(=O)c2cccnc2C(F)(F)F)ccc1O | 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 | null | null | To a solution of (4-hydroxy-3-methoxyphenyl)(2-(trifluoromethyl)pyridin-3-yl)methanone (0.472 g, 1.59 mmol) in acetic acid (10 mL) at room temperature was added 60% nitric acid (0.14 mL, 1.75 mmol) dropwise. The resulting mixture was allowed to stir for thirty minutes then poured onto ice-water (100 mL) and the resulti... | COc1cc(C(=O)c2cccnc2C(F)(F)F)cc([N+](=O)[O-])c1O | null | null | null |
1,480,421 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].Cl.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[C:30](=N)OCC.C(=O)([O-])O.[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[... | CCOC(=N)c1cccc(OC)c1 | Nc1cc(-c2nc3ccccc3o2)ccc1NC1CCOCC1 | null | Cl | O=C([O-])O | [Na+] | 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 | 25 | 8 | To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (200 mg, 0.646 mmol) in methanol (5 mL) was added ethyl 3-methoxybenzimidate hydrochloride (153 mg, 0.711 mmol), and this was stirred at room temperature for 8 hours. After the reaction was complete, saturated aqueous s... | COc1cccc(-c2nc3cc(-c4nc5ccccc5o4)ccc3n2C2CCOCC2)c1 | null | 78.6 | null |
1,735,254 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | [Cl:1][C:2]1[C:11](=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.P(Br)(Br)[Br:14]>CN(C=O)C>[Br:14][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[Cl:1] | O=c1c(Cl)c[nH]c2ccccc12 | BrP(Br)Br | 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 | 0 | 0.07 | To a cooled suspension of 3-chloroquinolin-4(1H)-one (A275-1) (5.15 g, 28.7 mmol) in DMF (43.4 mL) at 0° C. was added phosphorous tribromide (2.77 mL, 29.5 mmol) dropwise over 3 min and then the mixture became orange homogenous mixture. After 4 min, yellow precipitates were formed and the yellow heterogeneous mixture w... | Clc1cnc2ccccc2c1Br | null | null | null |
966,586 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=O)[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][C@@H:52]([CH2:66][C:67]1[CH:72]=[C:71]([F:73])[CH:70]=[C:69]([F:74])[CH:68]=1)[C@H:53]([OH:65])[CH2:54][NH:55][CH2:56][C:... | CCc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1 | CCCCn1ccc2ccc(C(=O)O)cc21 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | On1nnc2ccccc21 | 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 | 18 | To a mixture of 1-butyl-1H-indole-6-carboxylic acid (0.278 g) in methylene chloride (10 mL) was added triethylamine (0.129 g), HOBT (0.175 g) and, HATU (0.486 g). The mixture was stirred at room temperature for 30 minutes at which time (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.408 g) ... | CCCCn1ccc2ccc(C(=O)N[C@@H](Cc3cc(F)cc(F)c3)[C@H](O)CNCc3cccc(CC)c3)cc21 | null | 39.3 | null |
282,975 | ord_dataset-769fac6048e548eca2d49e48f972884b | null | 1994-01-01T00:01:00 | true | O[C:2]1[C:11]2[C:6](=CC(S(O)(=O)=O)=CC=2O)[CH:5]=[C:4](S(O)(=O)=O)[CH:3]=1.[NH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[C:30]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:29][CH:28]=[CH:27]2>>[NH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:31]=1[C:30]([S:32]([OH:35])(=[O:33])=[O:34])=[CH:29][CH:28]=[CH:27]2)[C:2]1[CH:... | Nc1cccc2cccc(S(=O)(=O)O)c12 | O=S(=O)(O)c1cc(O)c2c(O)cc(S(=O)(=O)O)cc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 4,5-dihydroxynaphthalene-2,7-disulfonic acid; 8-amino-1-naphthol-3,6-disulfonic acid; and 8-amino-1-naphthalene sulfonic acid. | O=S(=O)(O)c1cccc2cccc(Nc3ccccc3)c12 | null | null | null |
854,089 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [F:1][C:2]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7]>C(O)C.[Pd]>[F:1][C:2]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7] | O=C(O)C=Cc1cccc(F)c1F | null | null | [Pd] | 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 solution of 2,3-difluorocinnamic acid (9.14 g) in ethanol (250 ml) with 10% palladium/carbon catalyst was hydrogenated for 5 h at room temperature and atmospheric pressure. The reaction mixture was filtered through celite and concentrated in vacuo to give the title compound as a colourless solid (9.05 g, quant.) 1H-N... | O=C(O)CCc1cccc(F)c1F | null | 97.9 | null |
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