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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
797,856 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1Br)[CH:12]([NH:17][C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1)[CH2:11][CH2:10]2)=[O:5].[Cu][C:32]#[N:33].N>CN1C(=O)CCC1>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:... | N#C[Cu] | COCC(=O)Nc1cc2c(cc1Br)C(Nc1ccc(C(=O)OC(C)(C)C)cc1)CC2 | null | N | 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 | 25 | 2 | To a solution of tert-butyl 4-[N-(5-methoxyacetamido-6-bromoindan-1-yl)amino]benzoate (0.714 g, 1.50 mol) in NMP (8 ml) [1-methyl-2-pyrrolidone] was added copper (I) cyanide (0.230 g, 2.55 mmol). The reaction mixture was placed in an oil-bath preheated to 140° C. and stirred at this temperature for 2 h. More copper (I)... | COCC(=O)Nc1cc2c(cc1C#N)C(Nc1ccc(C(=O)OC(C)(C)C)cc1)CC2 | null | null | null |
726,031 | ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | null | 2006-01-01T00:08:00 | true | [CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:29]([NH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[NH2:43])([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[C:32]([O:31][C:29](=[O:30])[NH:36][C:37]1[CH:42]=[CH:4... | CC(C)(C)OC(=O)Nc1ccccc1N | C=CCN(CC=C)Cc1ccc(C(=O)O)s1 | null | O=C(n1ccnc1)n1ccnc1 | 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 | 0.75 | To a solution of 2.70 g (11.38 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid in 50 ml THF was added 2.03 g (12.51 mmol) carbonyldiimidazol. After 45 min at rt, 2.48 g (11.95 mmol) mono-boc-ortho-phenylenediamine were added to the reaction mixture, and it was stirred for 3 h at rt. The solvent was evaporated an... | C=CCN(CC=C)Cc1ccc(C(=O)Nc2ccccc2NC(=O)OC(C)(C)C)s1 | null | 84.3 | null |
1,370,799 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1>CN(C)C=O>[N:16]1[CH:17]=[CH:18][CH:19]=[N:20][C:15]=1[CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10] | Clc1ncccn1 | CCOC(=O)CC(=O)OCC | 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 | 4.80 g of sodium hydride (55% oil dispersion) was suspended in 50 ml of N,N-dimethylformamide. Into this, 17.60 g of diethyl malonate was added dropwise over a period of about 0.5 hours at room temperature under a nitrogen atmosphere. The mixture was stirred further for 0.5 hours at the same temperature, then, to the m... | CCOC(=O)C(C(=O)OCC)c1ncccn1 | null | 42.7 | null |
562,508 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | C([NH:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)[CH2:10]O)=[S:7])(C)(C)C.[ClH:22]>>[ClH:22].[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][C@H:9]1[CH2:10][S:7][C:6]([NH2:5])=[N:8]1)([O-:21])=[O:20] | CC(C)(C)NC(=S)N[C@H](CO)Cc1cccc([N+](=O)[O-])c1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 7 | The process is performed as in Example 2, starting with N-(tert-butyl)-N′-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea in 80 cm3 of aqueous 6N hydrochloric acid. The heating time is 7 hours. The product is isolated in an identical manner and then purified by chromatography under an argon pressure of 80 kPa, on a col... | NC1=N[C@@H](Cc2cccc([N+](=O)[O-])c2)CS1 | null | null | null |
1,126,688 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [C:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)(=O)[CH3:2].[CH2:19]([NH2:22])[CH2:20][NH2:21]>C(O)(=O)C>[NH2:21][CH2:20][CH2:19][NH:22][CH:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]... | NCCN | CCN(CC)C(=O)COc1ccc(C(C)=O)cc1 | 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 | By using 2-(4-acetylphenoxy)-N,N-diethylacetamide (250 mg), ethylenediamine (400 μl) and acetic acid (700 μl) as starting materials, the title compound (52.9 mg) was obtained in the same manner as that of Reference Example 64, (1). | CCN(CC)C(=O)COc1ccc(C(C)NCCN)cc1 | null | null | null |
294,858 | ord_dataset-bb4579c57ddc48c6a01fad97dacb6293 | null | 1994-01-01T00:08:00 | true | [CH2:1]([C:3]([CH2:22][CH3:23])([P:18]([OH:21])([OH:20])=[O:19])[C@H:4]1[CH2:13][CH2:12][C@@H:11]2[C@@H:6]([CH2:7][CH2:8][N:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)[CH2:5]1)[CH3:2].[CH3:24][OH:25]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.C([N+](CC)(CC)CC)C>[CH2:22]([C:3]([CH2:1][CH3:2])([P:18]([OH:20])([OH:21])=[O:19])[CH:4]1[... | CCC(CC)([C@H]1CC[C@H]2CN(C(=O)OC)CC[C@H]2C1)P(=O)(O)O | CO | null | CC[N+](CC)(CC)CC | Cc1ccc(S(=O)(=O)[O-])cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Four carbon plate electrodes were immersed into a solution containing the compound from Example 1 (250 mg), tetraethylammonium p-toluenesulfonate (21 mg), in methanol (10 ml). A constant current of 0.5 A was applied to the electrodes. Additional methanol (7.8 ml) was added to the reaction to replace methanol which was ... | CCC(CC)(C1CCC2CN(C(=O)OC)C(OC)CC2C1)P(=O)(O)O | null | null | null |
1,739,566 | ord_dataset-eacfee6d16d8455a93348409f1b37be4 | null | 2016-01-01T00:06:00 | true | C([O:4][C:5](=[O:26])[CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([N:19]([CH2:23][CH2:24][Cl:25])[CH2:20][CH2:21][Cl:22])=[CH:18][C:11]=2[N:10]=1)(C)C.[ClH:27]>O>[CH3:14][N:13]1[C:9]([CH2:8][CH2:7][CH2:6][C:5]([OH:26])=[O:4])=[N:10][C:11]2[CH:18]=[C:17]([N:19]([CH2:20][CH2:21][Cl:22])[CH2:23]... | CC(C)OC(=O)CCCc1nc2cc(N(CCCl)CCCl)ccc2n1C | null | null | Cl | 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 | 37.5 | 1 | 4-{5-[Bis-(2-chloroethyl)amino]-1-methyl-1H-benzimidazol-2-yl}-butyric acid isopropyl ester (3 g) is charged into a round bottom flask and 50% hydrochloric acid solution (21 mL) is slowly added. The mixture is heated to 35-40° C., maintained for about 90 minutes, and concentrated under vacuum at about 55-58° C., to giv... | Cn1c(CCCC(=O)O)nc2cc(N(CCCl)CCCl)ccc21 | null | null | null |
1,251,797 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | C[O:2][C:3](=[O:18])[CH:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)[CH:8]=1)[CH3:5].[Li+].[OH-].O1CCOCC1>>[N:13]1([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[O:6][CH:4]([CH3:5])[C:3]([OH:18])=[O:2])[CH:17]=[N:16][N:15]=[N:14]1 | COC(=O)C(C)Oc1cccc(-n2cnnn2)c1 | null | null | [Li+] | [OH-] | 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 | 3 | To a 25 mL round-bottom flask equipped with a magnetic stir bar was added 2-(3-tetrazol-1-yl-phenoxy)-propionic acid methyl ester 30 (326 mg, 1.3 mmol, 1.0 eq.), 2N LiOH (2.6 mL, 2.6 mmol, 2.0 eq), and 1,4-dioxane (2.6 ml, 2.6 mmol, 2.0 eq). The reaction mixture was then stirred at room temperature for 3 hours. The rea... | CC(Oc1cccc(-n2cnnn2)c1)C(=O)O | null | 75.6 | null |
815,804 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[OH:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8]>S(Cl)(Cl)=O>[C:7]([OH:9])(=[O:8])/[CH:6]=[CH:5]/[C:4]1[CH:10]=[CH:11][C:12]([OH:13])=[C:2]([OH:1])[CH:3]=1 | O=C(O)C=Cc1ccc(O)c(O)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 | 50 | 5 | 3,4-Dihydroxycinnamic acid (1.13 g, 6.27 mmole) was dissolved in thionyl chloride (25 ml) and the solution was stirred for 5 hours at 40-60° C. The solvent was removed, the residue was dissolved in thoroughly dried ethyl acetate and the solution was slowly added to a solution of 5-methoxy tryptamine (1.2 g) in benzene,... | O=C(O)/C=C/c1ccc(O)c(O)c1 | null | 60 | null |
372,730 | ord_dataset-ee5599340390470d8e5b5ac1feddf9d6 | null | 1997-01-01T00:08:00 | true | [C:1]([NH:4][CH:5]([O:16]CC)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].B(F)(F)F.CCOCC.O.C([O-])(O)=O.[Na+]>>[C:1]([NH:4][CH:5]([OH:16])[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])(=[O:3])[CH3:2] | CCOC(NC(C)=O)C(=O)NCc1ccccc1 | null | null | FB(F)F | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | O | null | null | null | null | null | null | null | null | null | null | null | Reacting 2-acetamido-N-benzyl-2-ethoxyacetamide (1.00 g, 4.0 mmol), BF3.Et2O (0.91 g, 6.4 mmol) and H2O (0.12 g, 6.7 mmol) followed by aqueous NaHCO3 workup gave an aqueous reaction mixture. The solution was then extracted with EtOAc (3×50 mL), and the combined EtOAc extracts were dried (Na2SO4), and concentrated in va... | CC(=O)NC(O)C(=O)NCc1ccccc1 | null | null | null |
868,169 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH3:13])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.[H-].[Na+].[CH3:20][S:21][CH2:22][CH2:23]Cl.O>CN(C=O)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:13])[CH2:23][CH2:22][S:21][CH3:20])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[... | CSCCCl | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.095 g, 0.32 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.015 g, 0.38 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then chloroethyl methyl sulfide (0.042 g, 0.38 mmol) was added in one portion as a solution in D... | CSCCN(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | 17.7 | null |
1,770,361 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [Br:1][C:2]1[S:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:9](=[O:10])[C:4]=2[C:3]=1[CH2:24]Br.CS(C)=[O:28]>CC(=O)OCC.O>[Br:1][C:2]1[S:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:1... | Cn1c(=O)n(CCCOC2CCCCO2)c(=O)c2c(CBr)c(Br)sc21 | CS(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of 6-bromo-5-(bromomethyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl) thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1.7 g, 3.43 mmol) in DMSO (20 mL) was added IBX (1.92 g, 6.85 mmol). The reaction was heated at 50° C. for 2 h, cooled to RT then diluted with EA (80 mL) and water (50 mL). The organic l... | Cn1c(=O)n(CCCOC2CCCCO2)c(=O)c2c(C=O)c(Br)sc21 | null | 33.8 | null |
1,385,553 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | [N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]#[N:15])[CH:8]=[CH:7][C:6]=2[C:5]1=[O:16])=[N+:2]=[N-:3].O.[BH4-].[Na+]>C1COCC1>[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]#[N:15])[CH:8]=[CH:7][C:6]=2[CH:5]1[OH:16])=[N+:2]=[N-:3] | N#Cc1ccc2c(c1)CCC(N=[N+]=[N-])C2=O | null | null | [BH4-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 0 | 0.75 | Racemic 6-azido-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (28 mg, 0.13 mmol) was dissolved in THF (1253 mL) and water (66.0 mL) at 0° C. To this solution was added sodium borohydride (6.49 mg, 0.17 mmol). The resulting solution was stirred at 0° C. for 45 min. After that, the reaction was quenched by several d... | N#Cc1ccc2c(c1)CCC(N=[N+]=[N-])C2O | null | 53.8 | null |
1,367,331 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | [I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[H-].[Na+].[CH2:9]1[CH2:13]O[CH2:11][CH2:10]1>>[CH2:13]([N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1)[CH2:9][CH2:10][CH3:11] | Ic1cn[nH]c1 | C1CCOC1 | null | [H-] | [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 | 70 | 8 | To a stirred suspension of 4-iodopyrazole (0.3 g, 1.55 mmol) and 60% NaH (0.08 g, 2 mmol) in anhydrous THF (1 ml) butyl bromide (0.5 ml) was added and the mixture was stirred overnight at 70° C. The mixture was quenched with saturated NH4Cl and extracted with EtOAc (50 ml). The organic layer was washed with H2O, dried ... | CCCCn1cc(I)cn1 | null | 100 | null |
628,938 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([OH:17])[CH:15]=2)[CH2:10][CH2:9][N:8]1[CH2:20][C:21]([NH:23][CH:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1)=[O:22].[CH2:38](Br)[CH2:39][CH2:40][CH3:41]>>[CH3:... | COc1cc2c(cc1O)C(Cc1ccc(OC)c(OC)c1)N(CC(=O)NC1CCc3ccccc31)CC2 | CCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | prepared by reaction of 2-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-(indan-1-yl)-acetamide with butyl bromide | CCCCOc1cc2c(cc1OC)CCN(CC(=O)NC1CCc3ccccc31)C2Cc1ccc(OC)c(OC)c1 | null | null | null |
658,546 | ord_dataset-be508e976bbb4586a0cc3368302a62f8 | null | 2005-01-01T00:01:00 | true | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C[Al](C)C.C([O:15][C:16]([C:18]1[NH:22][N:21]=[C:20]([CH3:23])[CH:19]=1)=O)C>C(Cl)Cl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([C:18]2[NH:22][N:21]=[C:20]([CH3:23])[CH:19]=2)=[O:15])=[N:3][CH:4]=1 | Nc1ccc(Br)cn1 | CCOC(=O)c1cc(C)n[nH]1 | null | C[Al](C)C | 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 | null | 4 | A solution of 2-amino-5-bromopyridine (0.200 g, 1.16 mmol 1.0 equiv), in 5 mls of methylene chloride, under argon, was treated with trimethylaluminum (0.312 mL, 2.0 N in hexanes, 4.0 equiv) at room temperature for 30 min. To the solution was added ethyl-3-methylpyrazole-5-carboxylate (0.356 g, 2.0 equiv). After 4 hrs, ... | Cc1cc(C(=O)Nc2ccc(Br)cn2)[nH]n1 | null | 49.1 | null |
176,670 | ord_dataset-07db50a3ce6941919df30a9e2898988f | null | 1988-01-01T00:08:00 | true | [OH:1][CH:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:3]1[C:8]2[S:9][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11](COC)[C:7]=2[CH:6]=[CH:5][N:4]=1.C[OH:28]>Cl>[OH:1][CH:2]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:3]1[C:8]2[S:9][C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11... | CO | COCc1c(-c2ccccc2)sc2c(C(O)c3ccccc3)nccc12 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 0.61 g (1.8 mmol) of 7-(hydroxyphenylmethyl)-3-methoxymethyl-2-phenyl-6-azabenzo[b]thiophene in 2.7 mL of 2M HCl and 2.7 mL of methanol was heated at reflux for 30 minutes. The solution was cooled and partitioned between ethyl acetate and water. The ethyl acetate layer was dried and concentrated to afford... | Oc1c(-c2ccccc2)sc2c(C(O)c3ccccc3)nccc12 | null | 93 | null |
516,790 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:5][CH:4]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20](... | COc1ccc(-c2[nH]c(-c3ccc([N+](=O)[O-])cc3)nc2C(=O)Nc2nccs2)cc1 | null | null | BrB(Br)Br | null | 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 | null | 24 | 5-(4-Methoxyphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (2.1 g) obtained in Example 47 was dissolved in dichloromethane (210 ml) and boron tribromide (3 ml) was added. The mixture was stirred for one day. The reaction mixture was poured into cold water and the precipitated crystals were collected ... | O=C(Nc1nccs1)c1nc(-c2ccc([N+](=O)[O-])cc2)[nH]c1-c1ccc(O)cc1 | null | 83.7 | null |
606,615 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | [C:1]1([CH:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([C:25](=[O:28])[NH:26][N:27]=4)[N:24]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C)... | CCOC(=O)CBr | O=c1[nH]nc2ccc(NCCCN3CCC(OC(c4ccccc4)c4ccccc4)CC3)nn12 | 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 | 1 | 0.550 g of 6-[3-[4-(diphenylmethoxy)piperidino]propylamino][1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one was suspended in 3 ml of N,N-dimethylformamide; 0.058 g of 60% oily sodium hydride was added, followed by stirring at room temperature for 1 hour. Under ice cooling, 0.160 ml of ethyl bromoacetate was added, followed by... | CCOC(=O)Cn1nc2ccc(NCCCN3CCC(OC(c4ccccc4)c4ccccc4)CC3)nn2c1=O | null | null | null |
1,354,861 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [CH2:1]([C:9]1[N:10]=[C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:14]3[N:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]2[CH:26]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>C1COCC1>[Br:27][C:26]1[N:12]2[C:13]3[CH:25]=[CH:24][CH:23]=[N:22][C:14]=3[NH:15][C:16]3[CH:21]=[CH:20][CH:19]=... | c1ccc(CCc2cn3c(n2)-c2ccccc2Nc2ncccc2-3)cc1 | O=C1CCC(=O)N1Br | 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 | 25 | 0.5 | To a solution 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.374 g, 1 eq.) in THF (50 mL) was added N-bromosuccinimide (0.206 g, 1.05 eq.). The reaction was stirred at room temperature for 30 minutes, poured onto water (100 mL) and extracted with dichloromethane (2×100 mL). The organic extracts wer... | Brc1c(CCc2ccccc2)nc2n1-c1cccnc1Nc1ccccc1-2 | null | 42.7 | null |
516,824 | ord_dataset-a495451286334c5c9bbcbd48a00c1350 | null | 2001-01-01T00:09:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]([O:22]C)=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[I-].[Li+].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20]([OH:22])=[O:21])(=[O:9])=[... | COC(=O)c1cc2ccccc2n1S(=O)(=O)c1cccc(Cl)c1 | null | null | Cl | [I-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | null | Methyl N-(3-chlorophenylsulphonyl)indole-2-carboxylate (0.56 g) and lithium iodide (2.0 g) were dissolved in pyridine and heated at reflux for 6 hours, cooled to room temperature and poured into 2M HCl and extracted with diethyl ether. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give an oi... | O=C(O)c1cc2ccccc2n1S(=O)(=O)c1cccc(Cl)c1 | null | 44.6 | null |
661,325 | ord_dataset-04d607efe1d9485eb99fafa06880f62e | null | 2005-01-01T00:02:00 | true | N1C=CC=CC=1.[NH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][N:20]([CH3:25])[S:21]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1)(=[O:23])=[O:22] | CN(C)S(=O)(=O)Cl | COC(=O)c1ccc(N)cc1Cl | null | CN(C)c1ccncc1 | null | 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 | 25 | 16 | Pyridine (0.4 mL) was added to a solution of methyl 4-amino-2-chlorobenzoate (0.3 g) in CH2Cl2 (10 mL) at 0° C. under N2. N,N-Dimethylsulfamoyl chloride (0.21 mL) was added and the mixture was stirred at room temperature for 16 hours and refluxed for 5 hours. DMAP (0.4 g) was added and the mixture was stirred for 3 hou... | COC(=O)c1ccc(NS(=O)(=O)N(C)C)cc1Cl | null | null | null |
1,211,261 | ord_dataset-dc3bb1b1ac4e4229a3fc28fb559a9777 | null | 2012-01-01T00:10:00 | true | [CH2:1]([O:4][CH2:5][C:6]([CH2:17][OH:18])([CH2:12][O:13][CH2:14][CH:15]=[CH2:16])[CH2:7][O:8][CH2:9][CH:10]=[CH2:11])[CH:2]=[CH2:3].[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23]>C1COCC1>[CH2:9]([O:8][CH2:7][C:6]([CH2:17][O:18][CH2:23][CH:22]=[CH2:21])([CH2:12][O:13][CH2:14][CH:15]=[CH2:16])[CH2:5][O:4][CH2:1][CH:2]=[CH2:3])... | C=CCOCC(CO)(COCC=C)COCC=C | C=CCBr | null | [H-] | [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 | 30.7 g (0.12 mol) of pentaerythritol triallylether was dissolved in 100 ml of dry THF and 4.4 g (0.18 mol) of NaH was added in small portions while stirring. After gas evolution had ceased, 16 ml (0.18 mol) of allyl bromide was added and the reaction mixture was stirred overnight at room temperature. In order to drive ... | C=CCOCC(COCC=C)(COCC=C)COCC=C | null | 99.2 | null |
1,353,569 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | Cl.[CH2:2]([O:9][CH:10]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C.C(OCC)C>[CH2:2]([O:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1 | CC(C)(C)OC(=O)N1CCC(OCc2ccccc2)C1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CCOCC | null | null | null | null | null | null | null | null | null | null | 0.25 | Hydrogen chloride (4N) in ethyl acetate (1.5 ml) was added to a solution of crude 3-benzyloxy-1-(tert-butoxycarbonyl)-pyrrolidine (705 mg) in diethyl ether (3 ml) and the mixture was stirred for 15 minutes. Reaction was quenched with water, and the solution was washed with diethyl ether. After addition of aqueous sodiu... | c1ccc(COC2CCNC2)cc1 | null | 40.4 | null |
318,030 | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | null | 1995-01-01T00:10:00 | true | [F:1][C:2]([F:13])([F:12])[C:3]1[O:4][C:5]([CH3:11])=[C:6]([C:8](=[O:10])[CH3:9])[N:7]=1.[BrH:14].BrBr>C(O)(=O)C>[F:13][C:2]([F:1])([F:12])[C:3]1[O:4][C:5]([CH3:11])=[C:6]([C:8](=[O:10])[CH2:9][Br:14])[N:7]=1 | CC(=O)c1nc(C(F)(F)F)oc1C | Br | null | BrBr | 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 | 80 | null | 5.8 g (0.02 mol) of 2-Trifluoromethyl-5-methyl-4-acetyl-oxazole are dissolved in 30 ml of glacial acetic acid, and 3 ml of a 33% strength solution of hydrogen bromide in glacial acetic acid are added. The mixture is heated to 80° C. and, over the course of 1 hour, a solution of 3.2 g (0.02 mol) of bromine in 10 ml of g... | Cc1oc(C(F)(F)F)nc1C(=O)CBr | null | null | null |
986,327 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[NH:31][C:32]([C@H:34]3[CH2:39][CH2:38][C@H:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:36][CH2:35]3)=[O:33])[C@H:14]2[CH3:46])[CH:6]=[C:7]... | CCOC(=O)C[C@H]1CC[C@H](C(=O)Nc2ccc(OC(F)(F)F)cc2CN2C(=O)O[C@H](c3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@@H]2C)CC1 | CCI | null | [H-] | [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 | Ethyl [trans-4-({[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl]amino}carbonyl)cyclohexyl]acetate (637 mg; 0-913 mmol) was treated with sodium hydride (60% in oil; 40 mg; 1.0 mmol) and iodoethane (110 mL; 1.37 mmol) as described in EXAMPLE 86 to aff... | CCOC(=O)C[C@H]1CC[C@H](C(=O)N(CC)c2ccc(OC(F)(F)F)cc2CN2C(=O)O[C@H](c3cc(C(F)(F)F)cc(C(F)(F)F)c3)[C@@H]2C)CC1 | null | null | null |
419,542 | ord_dataset-94e21e9990034c729ea727e7d2ab0eb0 | null | 1998-01-01T00:12:00 | true | [I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>CN(C=O)C.C(Cl)Cl>[I:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5] | O=C(O)c1ccccc1I | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | 2-Iodobenzoic acid (65.92 g, 0.266 mol), oxalyl chloride (40.5 g, 0.319 mol), CH2Cl2 (200 mL) and DMF (10 drops) were stirred at RT overnight. The reaction solution was concentrated, toluene was added and the solution concentrated to afford the crude 2-iodobenzoyl chloride. | O=C(Cl)c1ccccc1I | null | null | null |
1,653,875 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | F[C:2]1[C:9]([F:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][CH:15]([SH:17])[CH3:16]>CN(C=O)C.CCOC(C)=O>[F:10][C:9]1[C:2]([S:17][CH:15]([CH3:16])[CH3:14])=[C:3]([CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=1)[CH:4]=[O:5] | CC(C)S | O=Cc1cc([N+](=O)[O-])cc(F)c1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 1 | To a solution of 11A (51 mg, 0.273 mmol) in DMF (1 mL), were added TEA (0.057 mL, 0.409 mmol) and propane-2-thiol (0.030 mL, 0.327 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with H2O (2×), 10% LiCl and brine, dried (Na2SO4), filtered though a 1″ pad of SiO2 a... | CC(C)Sc1c(F)cc([N+](=O)[O-])cc1C=O | null | 96.3 | null |
1,509,238 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [NH2:1][C:2]1[C:7]([C@H:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]2[O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3OC)[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[C:17]([F:43])[CH:16]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[C:7]([C@H:8... | COc1ccc(CN(c2ccncn2)S(=O)(=O)c2cc(F)c(O[C@H]3CCCC[C@@H]3c3cccnc3N)cc2F)c(OC)c1 | null | 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 | ClCCl | null | null | null | null | null | null | null | null | null | null | null | The reaction and aftertreatment were conducted in the same manner as in Example 1b by using the 4-{[(1S*,2R*)-2-(2-aminopyridin-3-yl)cyclohexyl]oxy}-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (0.06 g, 0.09 mmol) prepared in Example 69c, triethylsilane (0.07 mL), trifluoroacetic acid (0.09... | Nc1ncccc1[C@H]1CCCC[C@@H]1Oc1cc(F)c(S(=O)(=O)Nc2ccncn2)cc1F | null | 82.3 | null |
1,602,715 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | C[O:2][C:3]([C:5]1[C:6]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:32])=O)=[CH:26][CH:25]=2)=[CH:7][CH:8]=[C:9]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=3)[N:15]=2)[CH:10]=1)=[O:4].[NH2:33][CH:34]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]1>>[Cl:23][C:18]1[CH:17]=[C:16... | COC(=O)c1cc(-c2nc(-c3ccc(Cl)c(Cl)c3)cs2)ccc1-c1ccc(C(=O)O)cc1 | CN1CCC(N)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 | Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described for Intermediate 8; 100 mg, 0.21 mmol) was reacted with 4-amino-1-methylpiperidine (available from Aldrich Chemical... | CN1CCC(NC(=O)c2ccc(-c3ccc(-c4nc(-c5ccc(Cl)c(Cl)c5)cs4)cc3C(=O)O)cc2)CC1 | null | 113.5 | null |
1,702,060 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[C:5]([F:16])=[C:4]([F:17])[CH:3]=1.[F:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[F:25]>>[F:18][C:19]1[CH:20]=[C:21]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[C:5]([F:16])=[C:4]([F:17])[CH:3]=2... | OB(O)c1ccc(F)c(F)c1 | O=C1NCCn2c1cc1c(F)c(F)cc(Br)c12 | null | null | null | null | null | null | null | 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, white solid (72 mg, 86%), MS (ISP) m/z=335.3 [(M+H)+], mp 317.5° C., was prepared in accordance with the general method of example 1 from 6-bromo-8,9-difluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 4) (75.3 mg, 0.25 mmol) and commercially available 3,4-difluoro-phenylboronic acid (5... | O=C1NCCn2c1cc1c(F)c(F)cc(-c3ccc(F)c(F)c3)c12 | null | null | null |
1,380,332 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[S:8][CH2:9][CH2:10][NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].[Cl:14][CH2:15][C:16](Cl)=[O:17]>C1COCC1.C(OCC)(=O)C>[Cl:14][CH2:15][C:16]([N:11]1[CH2:10][CH2:9][S:8][C:7]2[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]1=2)=[O:17] | O=C(Cl)CCl | O=[N+]([O-])c1ccc2c(c1)NCCS2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | C1CCOC1 | null | null | null | null | null | null | null | null | null | 60 | 0.17 | To a stirred solution of 6-nitro-3,4-dihydro-2H-benzo[b][1,4]thiazine (620 mg, 3.16 mmol) in THF (10 mL) was added 2-chloroacetyl chloride (0.277 mL, 3.48 mmol). The resulting mixture was then stirred at 60° C. for 10 minutes. The mixture was then diluted with ethyl acetate and washed with water (3×), 1:1 water:saturat... | O=C(CCl)N1CCSc2ccc([N+](=O)[O-])cc21 | null | 99.8 | null |
436,890 | ord_dataset-a1e9aa99368e4e5da8b1786b1c05521d | null | 1999-01-01T00:08:00 | true | O[CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:36]C(Br)(Br)Br>C(Cl)Cl>[Br:36][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11] | COC(=O)COc1cccc(CCCO)c1 | BrC(Br)(Br)Br | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | null | null | To a stirred solution of methyl 3-(3-hydroxypropyl)phenoxyacetate (2.00 g) in methylene chloride (20 ml) were added successively triphenylphosphine (2.81 g) and tetrabromomethane (3.55 g) at room temperature. The mixture was evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetat... | COC(=O)COc1cccc(CCCBr)c1 | null | 66 | null |
413,139 | ord_dataset-275344fd078b4340b89ca0b6e92beb95 | null | 1998-01-01T00:10:00 | true | [S:1]1[CH:5]=[CH:4][C:3]([SH:6])=[CH:2]1.[CH2:7]([C:11]1([CH2:14][CH3:15])[CH2:13][NH:12]1)[CH2:8][CH2:9][CH3:10]>>[NH2:12][C:11]([CH2:14][CH3:15])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][S:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1 | CCCCC1(CC)CN1 | Sc1ccsc1 | null | null | null | null | null | 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 | 15 | To a solution of n-butyl lithium in hexane (194 ml 1.6M) under nitrogen at -78° C. was added diethyl ether(120 ml) and then dropwise 3-bromothiophene (28 ml). The reaction was warmed to -30° C. and then cooled to -50° C. and powdered sulfur (10 g) was added. The reaction was stirred 15 hours at room temperature and the... | CCCCC(N)(CC)CSc1ccsc1 | null | 78.3 | null |
683,829 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1.[NH2:22][CH2:23][CH2:24][N:25]([CH3:34])[CH2:26][CH2:27][CH2:28][N:29]([CH2:31][CH2:32][NH2:33])[CH3:30]>ClCCl>[NH2:33][CH2:32][CH2:31][N:29]([CH3:30])[CH2:28][CH2:27][CH2:26][... | COc1ccc2c3c(c(Cl)nc2c1)C(=O)c1cnccc1-3 | CN(CCN)CCCN(C)CCN | null | null | 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 | 50 | 4 | A mixture of 6-chloro-3-methoxy-5,9-diaza-benzo[c]fluoren-7-one (50.8 mg) (the compound of Reference Example 1c-2) and N,N′-bis-(2-amino-ethyl)-N,N′-dimethyl-propane-1,3-diamine (0.5 ml) was stirred at 50° C. for 4 hours. The reaction mixture was diluted with dichloromethane. The solution was washed with saturated NaHC... | COc1ccc2c3c(c(NCCN(C)CCCN(C)CCN)nc2c1)C(=O)c1cnccc1-3 | null | null | null |
941,855 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH:16]1[CH2:33][CH:32]2[CH:18]([C:19](=[O:45])[N:20]([CH3:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][CH:27]3[C:29]([C:35]([NH:37][S:38]([CH:41]4[CH2:43][CH2:42]4)(=[O:40])=[O:39])=[O:36])([NH:30][C:31]2=[O:34])[CH2:28]3)[CH2:17]1.[CH:46]([C:49]1[N:50]=[C:51]([C:54]2[CH:63]=[... | COc1ccc2c(O)cc(-c3nc(C(C)C)cs3)nc2c1 | CN1CCCCC=CC2CC2(C(=O)NS(=O)(=O)C2CC2)NC(=O)C2CC(O)CC2C1=O | null | CC(C)OC(=O)/N=N/C(=O)OC(C)C | 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 | 8 | DIAD (22 uL, 0.11 mmol) was added to a mixture of the metathesis product 103 (23 mg), 2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxyquinolin-4-ol (24 mg, 0.08 mmol), and PPh3 (30 mg, 0.11 mmol) in 1 mL dry THF, in an ice bath. The mixture was stirred at rt overnight and then evaporated. The residue (1.2 mL of a 1.5-mL MeCN... | COc1ccc2c(OC3CC4C(=O)NC5(C(=O)NS(=O)(=O)C6CC6)CC5C=CCCCCN(C)C(=O)C4C3)cc(-c3nc(C(C)C)cs3)nc2c1 | null | 13 | null |
711,059 | ord_dataset-c8069773c1a148aca8ab417108daacc5 | null | 2006-01-01T00:05:00 | true | [CH2:1]([O:8][C@H:9]1[C@@:13]([CH2:16][O:17][C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)([CH2:14][OH:15])[O:12][C@@H:11]([N:41]2[CH:49]=[C:47]([CH3:48])[C:45](=[O:46])[NH:44][C:42]2=[O:... | COc1ccc(C(OC[C@]2(CO)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | Cc1ccc(S(=O)(=O)Cl)cc1 | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | 25 | 24 | To a solution of nucleoside 6 (2.79 g, 3.9 mmol) in anhydrous pyridine (50 cm3) was added a catalytic amount of 4-(N,N-dimethylamino)pyridine and p-toluenesulphonyl chloride (6.50 g, 34 mmol). The mixture was stirred in the dark for 24 h at room temperature under nitrogen. The reaction was quenched by addition of a sat... | COc1ccc(C(OC[C@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | 62.2 | null |
257,128 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [O:1]=[C:2]1[C:6]([CH2:7][S:8][C:9]2[CH2:10][S:11][C@@H:12]3[C@H:32]([NH:33]C(=O)CC4C=CC=CC=4)[C:31](=[O:43])[N:13]3[C:14]=2[C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[CH:5][CH2:4][O:3]1.CN1CCOCC1>ClCCl>[NH2:33][C@@H:32]1[C:31](=[O:43])[N:... | O=C(Cc1ccccc1)N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(SCC3=CCOC3=O)CS[C@H]12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CN1CCOCC1 | null | null | null | null | null | null | null | null | null | -30 | 0.5 | Diphenylmethyl 3-(2,5-dihydro-2-oxofuran-3-yl-methylthio)-7β-phenylacetamidoceph-3-em-4-carboxylate (0.83g) was dissolved in dichloromethane (11 ml) and treated with N-methylmorpholine (298μl). The atmosphere was purged with argon and the mixture cooled to -30° C. A solution of phosphorus pentachloride in dichlorometha... | N[C@@H]1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(SCC3=CCOC3=O)CS[C@H]12 | null | 89.6 | null |
1,605,178 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[CH3:16].CN(C)[CH:19]=[O:20]>CCCCC.C1COCC1>[CH3:16][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH:19]=[O:20])[CH:8]=2)[NH:12][N:11]=1 | CN(C)C=O | Cc1n[nH]c2ccc(Br)cc12 | null | [Li]C(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCCCC | null | null | null | null | null | null | null | null | null | null | 0.25 | Tetrahydrofuran (600 ml) was cooled down to −78° C. under argon atmosphere. At this temperature, a 1.7 M solution of tert-butyllithium in n-pentane (200 ml) was added dropwise. After 15 minutes at −78° C., a solution of 22.4 g (106.1 mmol) 5-bromo-3-methyl-1H-indazole in THF (300 ml) was added dropwise at such a rate t... | Cc1n[nH]c2ccc(C=O)cc12 | null | null | null |
886,561 | ord_dataset-d728a2f811c0424cbcdb5a84d02b93ae | null | 2009-01-01T00:06:00 | true | [F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[OH:10].C(N(CC)C(C)C)(C)C.Cl[CH2:21][O:22][CH3:23].Cl>ClCCl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH2:21][O:22][CH3:23] | COCCl | O=Cc1ccc(F)c(O)c1 | 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 | 3 | 4-Fluoro-3-hydroxybenzaldehyde (11.9 g) and N,N-diisopropylethylamine (44 mL) were dissolved in dichloromethane (100 mL). To the mixture was added chloromethylmethylether (13 mL), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added dropwise 1 mol/L hydrochloric acid (250 mL), ... | COCOc1cc(C=O)ccc1F | null | null | null |
1,322,185 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14])=[O:7].[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17].N12CCCN=C1CCCCC2>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]1[C:6](=[O:7])[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][C:16]1=[O:17] | COC(=O)CNC(=O)c1ccncc1N | O=C(n1ccnc1)n1ccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | C1CCC2=NCCCN2CC1 | null | null | null | null | null | null | null | null | null | null | 2 | To a solution of 100 mg of [(3-amino-pyridine-4-carbonyl)-amino]-acetic acid methyl ester in tetrahydrofuran (4.5 mL) is added 194 mg of 1,1′-carbonyldiimidazole and 0.18 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene at room temperature and the mixture is stirred at the same temperature for 2 h. Then the solvent is removed ... | COC(=O)Cn1c(=O)[nH]c2cnccc2c1=O | null | 88.9 | null |
1,605,348 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[C:9]1([C@@H:15]([NH2:17])[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:17][C@H:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:16])[CH:5]=[CH:6][CH:7]=1 | C[C@H](N)c1ccccc1 | Fc1cccc(Br)n1 | 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 | 100 | null | A mixture of 2-bromo-6-fluoropyridine (500 mg, 2.84 mmol) and (S)-(−)-1-phenylethylamine (0.435 mL, 3.41 mmol) were heated at 100° C. for 12 hours. The mixture was cooled to room temperature, dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purifi... | C[C@H](Nc1cccc(Br)n1)c1ccccc1 | null | null | null |
1,240,680 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.P(Cl)(Cl)(Cl)=O.CN([CH:20]=[O:21])C>>[F:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[C:7]=1[CH:20]=[O:21] | COc1cc(F)cc(OC)c1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 25 | 8 | To a solution of 1-fluoro-3,5-dimethoxybenzene (3.12 g, 20.0 mmol) in DMF (15 mL) was added dropwise phosphoryl trichloride (1.55 mL) at 0° C. The reaction mixture was stirred at room temperature overnight and poured onto ice. The resulting mixture was extracted with ethyl acetate (2×50 mL) and the combined organic lay... | COc1cc(F)c(C=O)c(OC)c1 | null | 74.6 | null |
386,610 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:11](O)[CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1>FC(F)(F)C(O)=O>[CH3:16][N:14]([CH3:15])[CH2:13][CH:12]=[CH:11][C:4]1[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=[C:2]([NH2:1])[CH:3]=1 | CN(C)CCC(O)c1cc(N)cc2c1OCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 1-(5-amino-2,3-dihydrobenzofuran-7-yl)-3-dimethylaminopropan-1-ol (D 16) (2.12 g) in trifluoroacetic acid (60 ml) was refluxed for 10h, cooled and the solvent evaporated under reduced pressure. The residue was partitioned between 10% Na2CO3 and ethyl acetate, the organic phase was dried (Na2SO4) and the s... | CN(C)CC=Cc1cc(N)cc2c1OCC2 | null | 105.7 | null |
1,592,717 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([CH:16]([NH:19][C:20]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)=[O:21])[CH2:17][CH3:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([N:27]1[C:28]2[C:24](=[CH:23][C:22]([C:20]([NH:19][CH:16]([C:10]3[CH:11]... | O=C(Cl)c1ccccc1 | CCC(NC(=O)c1ccc2[nH]ccc2c1)c1ccccc1 | 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 | null | null | Benzoyl chloride (1.1 equiv) was added to a solution of N-(1-phenylpropyl)-1H-indole-5-carboxamide in CH2Cl2, Et3N (1.3 equiv) at room temperature. After the reaction was completed, the solvent was evaporated and the residual was purified by silica gel column chromatography to get the product. LC-MS 383 (M+H). | CCC(NC(=O)c1ccc2c(ccn2C(=O)c2ccccc2)c1)c1ccccc1 | null | null | null |
1,697,663 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [CH3:1][O:2][N:3]([CH3:16])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N+:12]([O-:14])=[O:13].C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:11][C:7]1[C:6]([N+:12]([O-:14])=[O:13])=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([N:3]([O:2][CH3:1])[CH3:16])=[O:15] | CON(C)C(=O)c1cccc(C)c1[N+](=O)[O-] | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 80 | null | A mixture of Intermediate 37A (5.5 g, 24.53 mmol), NBS (5.24 g, 29.4 mmol) and benzoyl peroxide (0.594 g, 2.453 mmol) in CCl4 (80 mL) was purged with nitrogen and then heated to 80° C. for 4.5 h. The reaction mixture was cooled to room temperature and then quenched with water. The mixture was extracted with DCM and the... | CON(C)C(=O)c1cccc(CBr)c1[N+](=O)[O-] | null | null | null |
1,033,842 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:11][C@H:10]2[C:28]([N:30]2[CH2:33][C:32]([F:35])([F:34])[CH2:31]2)=[O:29])=[O:8])[CH2:5][CH2:4]1)#[N:2].Cl.[F:37][C:38]1([F:43])[CH2:42][CH2:41][NH:40][CH2:39]1>>[... | FC1(F)CCNC1 | N#CC1(NC(=O)[C@@H]2C[C@@H](S(=O)(=O)c3ccc(F)cc3C(F)(F)F)C[C@H]2C(=O)N2CC(F)(F)C2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in analogy to Example 127 using (1R,2R,4R)-2-(3,3-Difluoro-azetidine-1-carbonyl)-4-(4-fluoro-2-trifluoromethyl-benzenesulfonyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (Example 118) and 3,3-difluoropyrrolidine hydrochloride. Off-white solid. MS (EI): 611.2 (M+H)+. | N#CC1(NC(=O)C2CC(S(=O)(=O)c3ccc(N4CCC(F)(F)C4)cc3C(F)(F)F)CC2C(=O)N2CC(F)(F)C2)CC1 | null | null | null |
1,583,706 | ord_dataset-380e279f82154dba9e08ab51b3bdd08a | null | 2015-01-01T00:05:00 | true | [CH3:1][C:2]1[NH:3][C:4]2[N:5]([N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=2)[C:6](=O)[C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].O=P(Cl)(Cl)[Cl:25]>>[Cl:25][C:6]1[N:5]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=[C:4]2[N:3]=[C:2]([CH3:1])[C:7]=1[CH2:8][C:9]([O:11][CH3:1... | COC(=O)Cc1c(C)[nH]c2cc(-c3ccccc3)nn2c1=O | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0 | null | To methyl 2-(5-methyl-7-oxo-2-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate (3 g, 10.09 mmol) was added POCl3 (25 mL, 268 mmol). The reaction mixture was heated at reflux for 1 h. After cooling, the reaction mixture was added drop-wise to ice-water. A brown solid precipitated. The solid was filtered and washe... | COC(=O)Cc1c(C)nc2cc(-c3ccccc3)nn2c1Cl | null | 86.9 | null |
385,847 | ord_dataset-d330662edaed408d950898172aba7a4c | null | 1997-01-01T00:12:00 | true | [CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.Br[CH2:15]CO.Cl>C1COCC1>[Cl:12][C:7]1[CH:6]=[C:5]([CH:4]2[CH2:15][CH2:1][O:2][C:3]2=[O:13])[CH:10]=[CH:9][C:8]=1[Cl:11] | COC(=O)Cc1ccc(Cl)c(Cl)c1 | OCCBr | null | Cl | 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 | 45 | 2.5 | Heat [(CH3)3Si]2NLi (230 ml, 1.0M in THF) under N2 to 45° C. and add 3,4 dichlorophenyl acetic acid methyl ester (40 g, 0.183 moles) dissolved in 60 ml of dry THF dropwise over 2 h. Stir the solution at 45° C. for another 2.5 h. Cool the solution to room temperature, add a dry THF solution (30 ml.) of THP-protected Br(... | O=C1OCCC1c1ccc(Cl)c(Cl)c1 | null | null | null |
139,552 | ord_dataset-7d359d96b3a64882921ebdc6c850e22e | null | 1986-01-01T00:01:00 | true | [C:1]([NH:6][C:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:8]=1)(=O)[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([NH:6][C:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[N:8]=1)[CH2:2][CH... | CCCC(=O)NC1=NN(c2cccc(C(F)(F)F)c2)CC1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | According to the method of Example 1, 3-butyramido-1-(3-trifluoromethylphenyl)-2-pyrazoline was reduced with lithium aluminium hydride to produce 3-butylamino-1-(3-trifluoromethylphenyl)-2-pyrazoline which was a gum (yield 2.4 g) and was recrystallized as the hydrochloride m.p. 173.4° (yield 1.65 g). | CCCCNC1=NN(c2cccc(C(F)(F)F)c2)CC1 | null | null | null |
226,676 | ord_dataset-67612e25ea9d4b29966a776893a43d59 | null | 1991-01-01T00:04:00 | true | C([N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]([CH2:21][CH3:22])[C:12](=[O:23])[C:11]=2[N:10]=[CH:9]1)C1C=CC=CC=1>C(O)(=O)C.[C].[Pd]>[CH2:21]([N:13]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:20]2[NH:8][CH:9]=[N:10][C:11]=2[C:12]1=[O:23])[CH3:22] | CCn1c(=O)c2ncn(Cc3ccccc3)c2c2ccccc21 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | 70 | 3 | 3.0 g (0.0099 mol) of Compound e obtained in Reference Example 4 was dissolved in 110 ml of acetic acid. 0.89 g of 10% palladium carbon was added to the solution. Under hydrogen stream, the solution was stirred 3 hours at 70° C. After filtration, the filtrate was concentrated under reduced pressure. Anhydrous sodium ca... | CCn1c(=O)c2nc[nH]c2c2ccccc21 | null | 94.7 | null |
1,497,355 | ord_dataset-366bdd9ee72d474cbe6f3f9e54dd96d2 | null | 2014-01-01T00:10:00 | true | [C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[O:9]([CH2:16][C:17](O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>Cl>[O:9]([CH2:16][C:17]1[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1 | O=C(O)COc1ccccc1 | Nc1ccccc1N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 130 | 18 | A 100 mL flask fitted with a stir-bar and condenser was charged with 1,2-phenylenediamine (9.94 g, 92.1 mmol), phenoxyacetic acid (14.0 g, 92.1 mmol), and 4M HCl (140 mL). The suspension was heated in a 130° C. bath forming a green solution. After 18 hr, the reaction had gone to completion as monitored by HPLC. The mix... | c1ccc(OCc2nc3ccccc3[nH]2)cc1 | null | 89.6 | null |
1,717,965 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Br)=[CH:9][CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:19][C:20]([CH3:24])([CH3:23])[C:21]#[CH:22]>CN(C=O)C.[Cu](I)I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:2... | C#CC(C)(C)C | CCOC(=O)c1ccc(Br)s1 | null | I[Cu]I | [Pd] | O=C(/C=C/c1ccccc1)/C=C/c1ccccc1 | 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 | null | A mixture of 5-bromo-thiophene-2-carboxylic acid ethyl ester (7 g, 30 mmol), copper iodide (1.2 g, 6 mmol), triethylamine (20 mL) in DMF (100 mL) was degassed in a 350 mL pressure bottle. Then tris(dibenzylideneacetone)dipalladium(0) (2.1 g, 3 mmol) and 3,3-dimethyl-but-1-yne (18.3 mL, 150 mmol) were added and heated a... | CCOC(=O)c1ccc(C#CC(C)(C)C)s1 | null | 97.3 | null |
1,681,204 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][S:13][S:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCN=C=NCCCN(C)C>CC#N.CCOC(C)=O>[C:1]([NH:10][CH2:11][CH2:12][S:13][S:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:2... | O=C(O)c1cccnc1 | CC(C)(C)OC(=O)NCCSSCCN | null | CCN=C=NCCCN(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | CC#N | null | null | null | null | null | null | null | null | null | 25 | 4 | Separately, nicotinic acid (246 mg, 2.0 mmol) was taken up in CH3CN (10 mL) along with tert-butyl 2-(2-(2-aminoethyl)disulfanyl)ethylcarbamate (503 mg, 2.0 mmol), EDCI (422 mg, 2.2 mmol). The resulting reaction mixture was stirred at room temperature for 4 h and then diluted with EtOAc. The organic layer was washed wit... | CC(C)(C)OC(=O)NCCSSCCNC(=O)c1cccnc1 | null | 55.9 | null |
818,720 | ord_dataset-50f99930fc41474db226bc80774b38df | null | 2008-01-01T00:04:00 | true | C(OC([C:6]1[S:7][CH:8]=[C:9]2[C:14]=1[NH:13][C:12](=[O:15])[CH:11]=[C:10]2Cl)=O)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[CH2:17]([O:21][C:22]([C:11]1[C:12](=[O:15])[NH:13][C:14]2[C:9]([C:10]=1[N:27]1[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:20])(... | CCOC(=O)c1scc2c(Cl)cc(=O)[nH]c12 | CC(C)(C)OC(=O)N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In another method, intermediate 7-chloro-5-oxo-4,5-dihydro-2-thia-4-aza-indene-3-carboxylic acid ethyl ester, depicted by formula (25), was reacted with tert-butyl-1-piperazine carboxylate to yield 7-(4-tert-butoxycarbonyl-piperazin-1-yl)-5-oxo-4,5-dihydro-2-thia-4-aza-indene-6-carboxylic acid ethyl ester, depicted by ... | CCOC(=O)c1c(N2CCN(C(=O)OC(C)(C)C)CC2)c2cscc2[nH]c1=O | null | null | null |
1,322,902 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | Br[C:2]1[S:3][C:4]([C:7]([NH:9][CH2:10][C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([Cl:22])=[CH:17][CH:18]=3)[N:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:12]=2)=[O:8])=[CH:5][N:6]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CN1C(=O)CCC1>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[C:1... | O=C(NCc1cn(-c2ccccc2)c2cc(Cl)ccc2c1=O)c1cnc(Br)s1 | C1CCNCC1 | 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 | 120 | null | A mixture of 2-bromo-N-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methyl)-thiazole-5-carboxamide (intermediate F) (30 mg, 0.063 mmol) and piperidine (10.8 mg, 0.126 mmol) in NMP was heated to 120° C. in a sealed microwave tube. After heating for 2 hr., the mixture was allowed to cool to room temperature. The cr... | O=C(NCc1cn(-c2ccccc2)c2cc(Cl)ccc2c1=O)c1cnc(N2CCCCC2)s1 | null | null | null |
474,331 | ord_dataset-d56f0a7ec215495c92e641d9fa932d28 | null | 2000-01-01T00:09:00 | true | [F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]1[C:7]([C:8]([C:17]([O:19]C)=[O:18])=[CH:9][CH:10]=[CH:11]1)=[N:6]2>CO.O>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]1[C:7]([C:8]([C:17]([OH:19])=[O:18])=[CH:9][CH:10]=[CH:11]1)=[N:6]2 | COC(=O)c1cccc2cc3ccc(C(F)(F)F)cc3nc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | null | Cyclization of this as above, followed by immediate hydrolysis of the crude methyl 6-trifluoromethylacridine-4-carboxylate, gave 6-trifluoromethylacridine-4-carboxylic acid (81%), mp (MeOH/H2O) 244-246° C. 1H NMR [(CD3)2SO] δ 7.93 (t, J=7.9 Hz, 1 H, H-3), 7.98 (dd, J=8.9, 1.5 Hz, 1 H, ArH), 8.56 (d, J=8.8 Hz, 1 H, ArH)... | O=C(O)c1cccc2cc3ccc(C(F)(F)F)cc3nc12 | null | 81 | null |
900,149 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[NH:12]1[CH2:17][CH2:16][C:15](O)(O)[CH2:14][CH2:13]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH:14]=1 | OC1(O)CCNCC1 | COc1ccc2[nH]ccc2c1 | null | null | null | null | null | null | null | 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 experimental protocol used is described in the literature (Eur. J. Med. Chem. (1987) 22, 33-43), starting from 5-methoxy-1H-indole and 4,4-piperidinediol. | COc1ccc2[nH]cc(C3=CCNCC3)c2c1 | null | null | null |
262,576 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[O:11])=[C:8]([O:23][CH3:24])[CH:7]=1.N1C=CC=CC=1>C1C=CC=CC=1>[F:5][C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([Cl:3])=[O:15])=[O:11])=[C:8]([O:23][CH3:24])[CH:... | COc1cc(F)ccc1C(=O)c1ccccc1C(=O)O | O=S(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | Thionyl chloride (1.5 ml) was added to a solution of 2-(4-fluoro-2-methoxybenzoyl)benzoic acid (mp 119°-120° C.) (3.66 g) and pyridine (0.03 ml) in benzene (50 ml), followed by refluxing for an hour. The solvent was distilled off to give 2-(4-fluoro-2-methoxybenzoyl)benzoyl chloride (IRνmaxNujol : 1795 cm-1). A solutio... | COc1cc(F)ccc1C(=O)c1ccccc1C(=O)Cl | null | null | null |
577,308 | ord_dataset-a9ba4801408c4b01922886164c10a391 | null | 2003-01-01T00:01:00 | true | Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2.[CH2:24]([NH:26][CH2:27][CH2:28][OH:29])[CH3:25]>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([N:12]2[C:13]3[C:9](=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:26... | CCNCCO | Fc1cc2c(ccn2-c2ccc(Cl)cc2)cc1OCCCCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogy to example 23.7, 5-(4-Bromo-butoxy)-1-(4-chloro-phenyl)-6-fluoro-1H-indole and 2-(ethylamino)ethanol were converted to yield 2-({4-[1-(4-Chloro-phenyl)-6-fluoro-1H-indol-5-yloxy]-butyl}-ethyl-amino)-ethanol as a colorless oil, MS: 405 (MH+). | CCN(CCO)CCCCOc1cc2ccn(-c3ccc(Cl)cc3)c2cc1F | null | null | null |
300,918 | ord_dataset-9ad0840101374618a7d5c4e4521c82d1 | null | 1994-01-01T00:12:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12](O)[CH3:13])[CH2:11][O:10]1.[CH3:15][C:16]1[N:17]([C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])=[CH:24][CH:23]=2)[C:18](=[O:21])[NH:19][N:20]=1>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:10][CH2:11]1)... | C[C@H](O)[C@@]1(c2ccc(F)cc2F)CO1 | Cc1n[nH]c(=O)n1-c1ccc(OC(F)(F)C(F)F)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 | In the same manner as in Reference Example 5, starting from 0.50 g of (1S)-1-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 0.58 g of 5-methyl-4-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-3(2H,4H)-1,2,4-triazolone, 0.46 g of 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-5-methyl-4-[4-(1,1,2,2-tetrafluoroeth... | Cc1nn([C@H](C)[C@@]2(c3ccc(F)cc3F)CO2)c(=O)n1-c1ccc(OC(F)(F)C(F)F)cc1 | null | 48.8 | null |
956,639 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [NH2:1][CH2:2][C:3]1[N:4]=[C:5]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([C:22]3[NH:23][C:24]([CH3:29])=[C:25]([Cl:28])[C:26]=3[Cl:27])=[O:21])[CH2:15][CH2:14]2)[S:6][C:7]=1[C:8]([O:10]CC)=[O:9].[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31]>>[Cl:27][C:26]1[C:25]([Cl:28])=[C:24]([CH3:29])[NH:23][C:22]=1[C:20]([NH:19][CH:16... | CCN=C=O | CCOC(=O)c1sc(N2CCC(NC(=O)c3[nH]c(C)c(Cl)c3Cl)CC2)nc1CN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a manner analogous to Example 250 from ethyl 4-(aminomethyl)-2-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-thiazole-5-carboxylate (Example 246) and ethyl isocyanate. | CCNC(=O)NCc1nc(N2CCC(NC(=O)c3[nH]c(C)c(Cl)c3Cl)CC2)sc1C(=O)O | null | null | null |
249,827 | ord_dataset-4f3b2ca6df1d41ef8b5008f1f39da0e2 | null | 1992-01-01T00:06:00 | true | [Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH3:16][O:17][C:18]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:19]=1[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCCl>[CH3:16][O:17][C:18]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:11](=[O:12])[C:10]2[CH:14... | COc1ccc(C(=O)Cl)cc1 | CCOC(=O)CCc1ccc(OC)cc1OC | null | [Al+3] | [Cl-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | 0 | null | 52 g of aluminum trichloride are suspended in 200 ml of 1,2-dichloroethane and cooled to 0° C. Then, at this temperature, 66.5 g of 4-methoxybenzoyl chloride are added dropwise, followed by 94.7 g of ethyl 2,4-dimethoxyhydrocinnamate in 30 ml of 1,2-dichloroethane. The mixture is then heated at 50° C. with exclusion of... | CCOC(=O)CCc1cc(C(=O)c2ccc(OC)cc2)c(OC)cc1OC | null | null | null |
828,397 | ord_dataset-47bd90bf5ec74fcd99ce250a56e18c8f | null | 2008-01-01T00:07:00 | true | CN(CCN(C)C)C.C([Li])CCC.[Cl:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.CN([CH:24]=[O:25])C>CCOCC>[Cl:14][C:15]1[C:16]([CH:24]=[O:25])=[N:17][CH:18]=[CH:19][CH:20]=1 | Clc1cccnc1 | CN(C)C=O | null | CN(C)CCN(C)C | [Li]CCCC | 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 | 0.5 | To a solution of TMEDA (660 μL, 2.58 mmol) in ether (20 mL) at −78° C. was added a solution of n-butyl lithium in ether (2.5 M, 1.76 mL, 4.40 mmol). After 30 minutes at −78° C., 3-chloropyridine (419 μL, 4.40 mmol) was added. After another 2 hours at −78° C., DMF (375 μL, 4.84 mmol) was added. After a further 2 hours a... | O=Cc1ncccc1Cl | null | 27 | null |
1,479,385 | ord_dataset-c3c1091f873b4f40827973a6f1f9b685 | null | 2014-01-01T00:09:00 | true | [CH2:1]([O:3][C:4](=[O:14])[CH:5]([O:9][CH2:10][C:11]([CH3:13])=[CH2:12])[CH2:6]C=C)[CH3:2]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][CH:13]=[C:11]([CH3:12])[CH2:10][O:9]1)=[O:14])[CH3:2] | C=CCC(OCC(=C)C)C(=O)OCC | null | null | null | 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 | 0.83 | To a refluxing stirred solution of 2-(2-methyl-allyloxy)-pent-4-enoic acid ethyl ester (396 mg, 2.0 mmol) in CH2Cl2 (100 mL, 0.02 M solution) was added drop wise a solution of the tricyclohexylphosphine (1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)(benzylidine)ruthenium (IV)dichloride (85 mg, 0.1 mmol)... | CCOC(=O)C1CC=C(C)CO1 | null | 94 | null |
1,704,323 | ord_dataset-54347fcace774f89850681d6dec8009f | null | 2016-01-01T00:03:00 | true | [O:1]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])S(C(F)(F)F)(=O)=O.[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22]O.N1C=CC=CC=1>C(Cl)Cl>[Br:16][C:17]1[CH:21]=[CH:20][O:19][C:18]=1[CH2:22][O:1][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10] | OCc1occc1Br | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | c1ccncc1 | null | null | null | null | null | null | null | null | null | 0 | 1 | tert-Butyldimethylsilanyl triflate (17.13 g) was added slowly to a stirred, cooled solution of 3-bromo-2-hydroxymethylfuran (Intermediate 39, 10.1 g) in DCM (160 mL) and pyridine (9.57 g) while maintaining the temperature at 0° C. The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture w... | CC(C)(C)[Si](C)(C)OCc1occc1Br | null | 102.9 | null |
1,135,781 | ord_dataset-aaeaab5f3720492494c1cbbdd0ed2820 | null | 2012-01-01T00:02:00 | true | [CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:24](O)=[O:25])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[CH3:8].O[N:28]=[C:29]([NH2:31])[CH3:30]>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:10][CH:11]([C:24]3[O:25][N:31]=[C:29]([CH3:30])[N:28]=3)[... | Cc1ccc(C2CC(C(=O)O)CN(C(=O)N3CCC(O)CC3)C2)cc1C | CC(N)=NO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 200 mg (0.54 mmol) of the compound from Example 128A and 62 mg (0.81 mmol) of N′-hydroxyacetamidine were reacted according to the General Method 2. Yield: 154 mg (69% of theory) | Cc1noc(C2CC(c3ccc(C)c(C)c3)CN(C(=O)N3CCC(O)CC3)C2)n1 | null | null | null |
202,237 | ord_dataset-19e5fc80c1554f4f8641c835e055f02b | null | 1990-01-01T00:01:00 | true | [CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([NH:12][CH2:13][CH2:14][CH3:15])[CH2:10][CH3:11]>CCOCC>[CH2:9]([N:12]([CH2:13][CH2:14][CH3:15])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH3:11] | CCCNCCC | BrCc1ccccc1 | 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 | null | An 11.9 ml portion of benzyl bromide and 41 ml of dipropylamine in ether were reacted as described in Example 3, giving 17.6 g of N,N-dipropylbenzenemethanamine as a clear liquid. | CCCN(CCC)Cc1ccccc1 | null | null | null |
856,034 | ord_dataset-faa0236be76c4501841c954527cd1b6c | null | 2008-01-01T00:12:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:15][C@H:14]3[N:11]([C:12](=[O:19])[C@@H:13]3[C@H:16]([OH:18])[CH3:17])[C:10]=2[C:20]([O-:22])=[O:21])=[CH:5][CH:4]=1)#[N:2].[Na+].Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:... | ClCCN1CCOCC1 | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)[O-])=C(c3ccc(C#N)cc3)C[C@H]12 | null | CCCC[N+](CCCC)(CCCC)CCCC | [I-] | [Na+] | 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 | Sodium (5R,6S)-3-(4-cyanophenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.2 g) in dry DMF (4.0 ml) was ice-cooled. Thereto ware added tetrabutylammonium iodide (0.53 g), and 4-(2-chloroethyl)-morpholine (1M toluene, 8 mL), and the mixture was stirred. Thirty minutes later, after remo... | C[C@@H](O)[C@H]1C(=O)N2C(C(=O)OCCN3CCOCC3)=C(c3ccc(C#N)cc3)C[C@H]12 | null | 33 | null |
1,527,491 | ord_dataset-8c74302143c04eb9983e4b3a7ead2d72 | null | 2014-01-01T00:12:00 | true | [N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].OS(O)(=O)=O>>[F:5][C:6]1[CH:16]=[C:15]([F:17])[C:14]([N+:1]([O-:4])=[O:2])=[CH:13][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9] | CCOC(=O)c1ccc(F)cc1F | O=[N+]([O-])O | null | O=S(=O)(O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 2 | Conc. HNO3 (8 mL) was added dropwise to a mixture of ethyl 2,4-difluorobenzoate (10.0 g; 53.7 mmol) in cone. H2SO4 (8 mL) at 0° C. After 2 h at 0° C., the mixture was poured onto ice and extracted with EtOAc. The organic extracts were washed with saturated NaHCO3 solution (aq) and concentrated to give the sub-title com... | CCOC(=O)c1cc([N+](=O)[O-])c(F)cc1F | null | null | null |
1,140,030 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[CH3:9][CH:10]1[CH2:15][CH:14]([CH3:16])[CH2:13][NH:12][CH2:11]1>>[Cl:8][C:6]1[CH:7]=[C:2]([N:12]2[CH2:13][CH:14]([CH3:16])[CH2:15][CH:10]([CH3:9])[CH2:11]2)[N:3]=[CH:4][N:5]=1 | Clc1cc(Cl)ncn1 | CC1CNCC(C)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 5 | 0.3 g of 4,6-dichloropyrimidine and 0.34 g of 3,5-dimethylpiperidine (cis/trans diastereomer=about 3/1) were mixed and left for 5 hours at room temperature. The reaction mixture was subjected to silica gel column chromatography to obtain 0.3 g of 4-chloro-6-(3,5-dimethylpiperidino)pyrimidine. This compound had the cis/... | CC1CC(C)CN(c2cc(Cl)ncn2)C1 | null | 66 | null |
1,146,392 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [S:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]4[N:17]5[N:18]=[C:19]([C:22]6[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=6)[CH:20]=[N:21][C:16]5=[N:15][N:14]=4)[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.O.[OH-].[Li+].Cl>CO.O>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]4[N:17]5[N:18]=[C:19]([C:22]6[CH:31]=[C... | COC(=O)c1ccc(-c2cnc3nnc(C4(c5ccc6ncsc6c5)CC4)n3n2)cc1 | null | null | Cl | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | 25 | 4 | A mixture of methyl 4-{3-[1-(1,3-benzothiazol-6-yl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl}benzoate (80.0 mg, 0.19 mmol) and lithium hydroxide monohydrate (16.0 mg, 0.37 mmol) in methanol (3.0 mL) and water (1.0 mL) was stirred at RT for 4 h. The mixture was adjusted with 1N HCl to pH=5. The volatiles wer... | O=C(O)c1ccc(-c2cnc3nnc(C4(c5ccc6ncsc6c5)CC4)n3n2)cc1 | null | null | null |
973,109 | ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | null | 2010-01-01T00:06:00 | true | [C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8](OC(=N)C(Cl)(Cl)Cl)[O:7][CH:6]1[CH2:26][O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2].[Cl:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36]([Cl:53])[C:37]=1[NH:38][C:39]1[C:48]2[C:43](=[C:44]([OH:51])[C:45]([O:49][CH3:50])=[CH:4... | CC(=O)OCC1O[C@H](OC(=N)C(Cl)(Cl)Cl)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)oc2c1O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 25 | 2 | Boron trifluoride•OEt2 (54 μL, 0.43 mmol) was added to a suspension of (3R,4S,5S,6R)-2-(acetoxymethyl)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.168 g, 0.341 mmol), 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one (60 mg, 0.17 mmol, Example 29), and anhydrous a... | COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)oc2c1O[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O | null | null | null |
9,377 | ord_dataset-ad879e603f9440f6bfb7fbd18e5e8761 | null | 1976-01-01T00:06:00 | true | [CH3:1][O:2][C:3]([CH3:19])([CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:17])[CH2:8][CH:9]=[CH:10][CH:11]=[C:12]([CH3:16])[C:13]([OH:15])=[O:14].[CH2:20](Br)[C:21]#[CH:22]>>[CH2:22]([O:14][C:13](=[O:15])[C:12]([CH3:16])=[CH:11][CH:10]=[CH:9][CH2:8][CH:7]([CH3:17])[CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH3:18])[CH3:19])... | COC(C)(C)CCCC(C)CC=CC=C(C)C(=O)O | C#CCBr | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Utilizing the procedure of Example 15, 11-methoxy-2,7,11-trimethyl-2,4-dodecadienoic acid and propargyl bromide are reacted. After chromatography on Kieselgel, using diethyl ether/petroleum ether (1:3 parts by volume) as the eluant, there is obtained 11-methoxy-2,7,11-trimethyl-2,4-dodecadienoic acid propargyl ester in... | C#CCOC(=O)C(C)=CC=CCC(C)CCCC(C)(C)OC | null | null | null |
109,744 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | [CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[C:4]=1[C:14]([F:17])([F:16])[F:15].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[C:4]2[C:14]([F:16])([F:15])[F:17] | COc1ccc2c(C)cccc2c1C(F)(F)F | O=C1CCC(=O)N1Br | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | A suspension of 2-methoxy-5-methyl-1-(trifluoromethyl)naphthalene (1.2 g, 5.0 mmol), N-bromosuccinimide (1.07 g, 6.0 mmol) and benzoyl peroxide (20-30 mg) in carbon tetrachloride (10 mL) was heated at reflux for 1.5 hr. The residual solid in the reaction mixture was removed by filtration, and the collected solid on the... | COc1ccc2c(CBr)cccc2c1C(F)(F)F | null | 106.5 | null |
91,875 | ord_dataset-dba7c8cf38834984ba5e6376158f46fe | null | 1982-01-01T00:03:00 | true | Br[CH2:2][CH:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CC(C)([O-])C.[K+].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>C(O)CCC>[CH:3]1([CH2:2][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1 | c1c[nH]cn1 | BrCC1CCCCCC1 | null | CC(C)(C)[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCO | null | null | null | null | null | null | null | null | null | null | null | 7 | Bromomethylcycloheptane (5.3 g, 0.0278 mol) was added dropwise to a stirred solution of potassium t-butoxide (3.1 g, 0.0277 mol) and imidazole (1.9 g, 0.0279 mol) in dry n-butanol (50 ml) maintained at 100° and under dry nitrogen. After the addition (~20 mins) the temperature of the reaction mixture was raised to boili... | c1cn(CC2CCCCCC2)cn1 | null | null | null |
999,943 | ord_dataset-70899a0178cc441482746c093624afa0 | null | 2010-01-01T00:10:00 | true | [CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][CH:6]=1)[CH3:2].C([Li])(CC)C.[CH3:22][S:23]SC>C1COCC1>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH3:13])=[CH:7][C:6]=1[S:23][CH3:22])[CH3:16] | CCCc1ccc(C(=O)N(CC)CC)cc1 | CSSC | null | [Li]C(C)CC | 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 | 0.5 | To a stirring solution of N,N-diethyl-4-propylbenzamide (2.0 g, 9.3 mmol) and N,N,N′N′-tetramethylethylenediamine (1085 mg, 9.4 mmol) in dry THF (93 mL) at −78° C. under Ar was added 0.78 M s-butyllithium in hexanes (12 mL). The reaction was stirred for 30 min and then methyl disulfide (1936 mg, 12.1 mmol) was added. T... | CCCc1ccc(C(=O)N(CC)CC)c(SC)c1 | null | 85.1 | null |
193,789 | ord_dataset-b83b16f2fb1a4f8782f3d82c1766cc6b | null | 1989-01-01T00:08:00 | true | [CH2:1]([N:8]([C:13]1[N:21]=[CH:20][N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2C1CCCCO1)[CH2:9][CH:10]([CH3:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N>O>[CH2:1]([N:8]([C:13]1[N:21]=[CH:20][N:19]=[C:18]2[C:14]=1[NH:15][CH:16]=[N:17]2)[CH2:9][CH:10]([CH3:12])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=... | CC(C)CN(Cc1ccccc1)c1ncnc2c1ncn2C1CCCCO1 | null | null | Cl | N | 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 | 8 | A solution of 17.0 g. (47 mmole) 6-[N-benzyl-N-(2-methylpropyl)-amino]-9-tetrahydropyran-2-ylpurine (compound of Example 1) in 200 ml. saturated ethanolic hydrogen chloride solution is heated under reflux for 10 minutes. After standing overnight, the reaction mixture is diluted with water, adjusted to pH 7 with aqueous... | CC(C)CN(Cc1ccccc1)c1ncnc2nc[nH]c12 | null | 80 | null |
321,498 | ord_dataset-eed8d32c2f1d46a89ba39d04dfaa83b1 | null | 1995-01-01T00:12:00 | true | CCN(S(F)(F)[F:7])CC.[C:10]([O:14][P:15]([CH:22](O)[C:23]1[CH:45]=[CH:44][C:26]([CH2:27][CH:28]([C:40]([O:42][CH3:43])=[O:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:25][CH:24]=1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(Cl)(Cl)Cl.[Cl... | COC(=O)C(Cc1ccc(C(O)P(=O)(OC(C)(C)C)OC(C)(C)C)cc1)NC(=O)OCc1ccccc1 | CCN(CC)S(F)(F)F | null | [Cl-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To DAST (0.15 mL, 1.1 mmol) in anhydrous CHCl3 (0.6 mL) at -78° C. was slowly added compound 9 (536 mg, 1.0 mmol) in CHCl3 (2.0 mL). After 10 minutes, the reaction mixture was warmed to ambient temperature and stirred (20 minutes). The mixture was slowly diluted with brine (10 mL) then extracted with CHCl3 (2×10 mL) an... | COC(=O)C(Cc1ccc(C(F)P(=O)(OC(C)(C)C)OC(C)(C)C)cc1)NC(=O)OCc1ccccc1 | null | 117 | null |
1,658,694 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[CH:4][C:3]=1[C:16]1[NH:17][C:18]2[C:19]([N:27]=1)=[N:20][CH:21]=[C:22]([N+:24]([O-])=O)[CH:23]=2.O.O.Cl[Sn]Cl>C(O)C>[NH2:24][C:22]1[CH:23]=[C:18]2[NH:17][C:16]([C:3]3[CH:4]=[C:5]([NH:8][C:9]([C:11]4[O:12][CH:13]=[CH:14][CH:15]=4)... | O=C(Nc1ccc(Cl)c(-c2nc3ncc([N+](=O)[O-])cc3[nH]2)c1)c1ccco1 | null | null | Cl[Sn]Cl | null | 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 | To a suspension of N-(4-chloro-3-[6-nitro-1H-imidazo[4,5-b]pyridin-2-yl]phenyl)furan-2-carboxamide (3.9 g, 10.16 mmol, 1.00 equiv) in ethanol (50 mL) was added SnCl2.2H2O (3.4 g, 15.04 mmol, 1.48 equiv) and heated to reflux overnight. The reaction mixture was concentrated under vacuum and diluted with H2O. The pH value... | Nc1cnc2nc(-c3cc(NC(=O)c4ccco4)ccc3Cl)[nH]c2c1 | null | 54.3 | null |
1,621,169 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [CH:1]1([NH:4][C:5]2[S:9][C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[N:7][CH:6]=2)[CH2:3][CH2:2]1.[Cl:16]N1C(=O)CCC1=O>C(#N)C>[Cl:16][C:6]1[N:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:9][C:5]=1[NH:4][CH:1]1[CH2:3][CH2:2]1 | c1cncc(-c2ncc(NC3CC3)s2)c1 | O=C1CCC(=O)N1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | 0 | 1 | To a solution of N-cyclopropyl-2-(pyridin-3-yl)thiazol-5-amine (1.00 g, 4.60 mmol) in acetonitrile (2 mL) was added 1-chloropyrrolidine-2,5-dione (645 mg, 4.83 mmol) and the mixture stirred at 0° C. for 1 h. The mixture was filtered and the filtrate was treated with excess HCl (4M in dioxane) to give 4-chloro-N-cyclopr... | Clc1nc(-c2cccnc2)sc1NC1CC1 | null | null | null |
1,101,768 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[S:18][C:19]([C:29]([NH2:31])=[O:30])=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:21]=3)[C:13]=2[CH:32]=1)C1C=CC=CC=1.ClCCl>O>[Cl:28][C:24]1[CH:23]=[C:22]([C:20]2[N:21]=[C:17]([N:14]3[C:13]4[CH:32]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=4[N... | NC(=O)c1sc(-n2cnc3ccc(OCc4ccccc4)cc32)nc1-c1cccc(Cl)c1 | null | null | null | null | 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 | 1 | To a mixture of 3.2 g (6.96 mmole) of 2-(6-benzyloxy-benzoimidazol-1-yl)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (I.25c) and 50 mL of dichloromethane at 0 degrees was added, dropwise, 5.86 mL (56 mmole) of boron trifluoride-dimethylsulfide complex. The mixture was stirred at ambient temperature for 1 hour ... | NC(=O)c1sc(-n2cnc3ccc(O)cc32)nc1-c1cccc(Cl)c1 | null | 100.7 | null |
1,418,317 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:7]=3[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][... | CC(C)(C)OC(=O)N1CCc2c([nH]c3cc(Br)ccc23)C1 | CI | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | ClCCl | null | null | null | null | null | null | null | null | null | null | 0.5 | tert-Butyl 7-bromo-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (1.96 g, 5.58 mmol) was dissolved in DMF (20 mL), and sodium hydride (60% weight dispersion in mineral oil, 330 mg, 8.37 mmol) was added. After 30 minutes, methyl iodide (0.52 mL, 8.4 mmol) was added, and the reaction stirred for a further 2 h. The... | Cn1c2c(c3ccc(Br)cc31)CCN(C(=O)OC(C)(C)C)C2 | null | 85.9 | null |
1,626,813 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:28][CH2:27][CH:26]([NH:29]C(=O)OC(C)(C)C)[CH2:25]2)=[N:22][CH:23]=1.[Cl:37][C:38]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[C:40]([F:53])[C:39]=1[OH:54]>>[NH2:... | CC1(C)OB(c2cc(F)c(O)c(Cl)c2)OC1(C)C | CC(C)(C)OC(=O)NC1CCN(c2ccc(Nc3c(C(=O)C4CC4)cnc4ccc(Br)cc34)cn2)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following general procedure D, tert-butyl 1-(5-(6-bromo-3-(cyclopropanecarbonyl)quinoline-4-ylamino)pyridin-2-yl)pyrrolidin-3-ylcarbamate (100 mg, 0.18 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (74 mg, 0.27 mmol) to obtain the protected intermediate which was subject... | NC1CCN(c2ccc(Nc3c(C(=O)C4CC4)cnc4ccc(-c5cc(F)c(O)c(Cl)c5)cc34)cn2)C1 | null | 22.5 | null |
732,498 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[O:13][N:12]=[C:11]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[NH2:25]>>[CH3:32][O:31][C:27]1[CH:26]=[C:24]([NH:25][C:2]2[N:7]=[C:6]([NH:8][C:9]3[O:13][N:12]=[C... | Clc1nccc(Nc2cc(C3CCCCC3)no2)n1 | COc1cc(N)cc(OC)c1OC | null | null | null | null | null | null | null | 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 by the method described in Example 1 using 2-chloro-N4-(3-cyclohexylisoxazol-5-yl)-4-pyrimidineamine (Step C) and 3,4,5-trimethoxyaniline. MS (MH+)=426.5; Calc'd for C22H27N5O4— 425.49. | COc1cc(Nc2nccc(Nc3cc(C4CCCCC4)no3)n2)cc(OC)c1OC | null | null | null |
41,820 | ord_dataset-48929f64ce614f1181a555eafd7c97a6 | null | 1978-01-01T00:06:00 | true | [C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]1[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([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.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[C:1]([S:20][C@@H:21]1[O:29][C@H:... | OC[C@H]1O[C@@H](SC(c2ccccc2)(c2ccccc2)c2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 22 | S-Trityl-1-thio-β-D-glucopyranose (3.6 g.) was dissolved in 50 ml. dry pyridine, cooled to 0° while 5 ml. (7.5 g.) of methylsulfonyl chloride was added. The solution was placed in the refrigerator for 22 hours until thin layer chromatography showed only traces of starting material or partially reacted products remainin... | CS(=O)(=O)OC[C@H]1O[C@@H](SC(c2ccccc2)(c2ccccc2)c2ccccc2)[C@H](OS(C)(=O)=O)[C@@H](OS(C)(=O)=O)[C@@H]1OS(C)(=O)=O | null | null | null |
149,489 | ord_dataset-f222e615b1f74f0fabef9cd9b98516b7 | null | 1986-01-01T00:10:00 | true | [OH:1][CH:2]1[CH2:6][CH2:5][O:4][CH2:3]1.C(N(CC)CC)C.[N+:14]([C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=2[Cl:37])=[CH:22][C:18]=1[C:19](Cl)=[O:20])([O-:16])=[O:15]>C1(C)C=CC=CC=1>[N+:14]([C:17]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:3... | OC1CCOC1 | O=C(Cl)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | 8 | 3-Hydroxytetrahydrofuran (1.76 grams; 0.02 mole), toluene (50 ml) and triethylamine (2.0 grams; 0.02 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. A solution of 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)benzoyl chloride (7.60 grams; 0.02 mole) in toluene (10 ... | O=C(OC1CCOC1)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-] | null | null | null |
1,612,462 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[C@H:14]([OH:25])[CH2:15][S:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])=[CH:4][CH:3]=1.[CH2:26]([O:28][C:29]([C:31]1([C:34]2[CH:39]=[CH:38][C:37](B3OC(C)(C)C(C)(C)O3)=[CH:36][CH:35]=2)[CH2:33][CH2:32]1)=[O:30])[CH3:27]>>[CH2:26... | CCOC(=O)C1(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1 | Cc1noc(-c2ccc(Br)cc2)c1[C@H](O)CS(=O)Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared according to the procedure described in Example 110, Step 3, using (S)-1-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-2-phenylmethanesulfinyl-ethanol and 1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester. | CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4[C@H](O)CS(=O)Cc4ccccc4)cc3)cc2)CC1 | null | null | null |
797,445 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | [CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=2[NH2:25])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1(C)C=CC(S(O)(=O)=O)=CC=1>COC(OC)OC>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24]... | CS(=O)(=O)c1ccc(NC2CCN(Cc3ccccc3)CC2)c(N)c1 | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COC(OC)OC | null | null | null | null | null | null | null | null | null | null | null | null | The crude material from step 2 (130 g) was stirred in 300 mL trimethylorthoformate containing 4-toluenesulphonic acid (8 g) at 90° C. for one hour, and collecting the methanol distillate. The reaction was cooled and filtered to give 108 g 1-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazole as a brown solid. | CS(=O)(=O)c1ccc2c(c1)ncn2C1CCN(Cc2ccccc2)CC1 | null | 629.2 | null |
1,327,207 | ord_dataset-cfad8b3f00044bcda60a96b019f09872 | null | 2013-01-01T00:08:00 | true | [CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]#[C:12][Si](C)(C)C)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:11]([C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([CH3:1])=[N:3][CH:4]=1)#[CH:12] | Cc1ncc(C#C[Si](C)(C)C)cc1[N+](=O)[O-] | 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 | 0.17 | A solution of 2-methyl-3-nitro-5-[(trimethylsilyl)ethynyl]pyridine (2.32 g, 9.90 mmol) in methanol (22 mL) was cooled to 0° C. and potassium carbonate (137 mg, 0.99 mmol) was added. The reaction mixture was allowed to warm and stir at rt for 10 min, during which time a yellow precipitate formed. The reaction mixture wa... | C#Cc1cnc(C)c([N+](=O)[O-])c1 | null | 92.2 | null |
1,447,008 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | I[C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][O:8][C:4]=2[CH:3]=1.OC1C=CC([I:25])=CC=1C(OC)=O>>[I:25][C:13]1[CH:2]=[CH:3][C:4]2[O:8][CH:7]=[C:6]([CH2:9][CH2:10][NH2:11])[C:5]=2[CH:12]=1 | NCCc1coc2cc(I)ccc12 | COC(=O)c1cc(I)ccc1O | null | null | null | null | null | null | null | 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 as described for 2-(6-iodo-1-benzofuran-3-yl)ethanamine using methyl 2-hydroxy-5-iodobenzoate. 1H-NMR (400 MHz, DMSO-d6): δ 2.91 (t, J=7.7 Hz, 2H), 3.11 (m, 2H), 7.45 (d, J=8.5 Hz, 1H), 7.65 (dd, J=8.5, 1.8 Hz, 1H), 7.90 (s, 1H), 8.09 (bs, 2H), 8.11 (d, J=1.7 Hz, 1H). | NCCc1coc2ccc(I)cc12 | null | null | null |
336,351 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | [ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C@@H:12]([CH2:14][OH:15])[C@@H:11]([NH:16][CH2:17][CH:18]=[CH2:19])[CH2:10][CH2:9]2.[H][H]>[Pd].C(O)C>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C@@H:12]([CH2:14][OH:15])[C@@H:11]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2 | C=CCN[C@H]1CCc2cccc(OC)c2[C@H]1CO | [H][H] | null | [Pd] | Cl | 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 | The mixture of 0.99 g (4.0 mmol) of cis-(+-)-1,2,3,4-tetrahydro-8-methoxy-2-(2-propenylamino)-1-naphthalenemethanol hydrochloride, 0.5 g 10% Palladium on carbon, and 80 mL of 95% ethanol was shaken in a Parr shaker apparatus under 50 p.s.i. of hydrogen atmosphere. After 18 hours, the mixture was filtered through a Celi... | CCCN[C@H]1CCc2cccc(OC)c2[C@H]1CO | null | null | null |
934,735 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH2:22][CH2:23][C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]([C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34])([CH3:30])([CH3:29])[CH3:28].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>... | CC(C)(C)OC(=O)Nc1cc(Oc2cccc(CCC(=O)O)c2)ccn1 | CC(C)(C)c1cccc(N)c1 | null | CCN=C=NCCCN(C)C | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 18 | To a solution of 3-[3-({2-[(tert-butoxycarbonyl)amino]pyridin-4-yl}oxy)phenyl]propanoic acid (333 mg, 0.93 mmol) in DCM (10 mL), were added 3-tert-butylaniline (152 mg, 1.02 mmol), DMAP (125 mg, 1.02 mmol) and then EDCI (196 mg, 1.02 mmol). The reaction was stirred for 18 h., and then diluted with DCM and washed with w... | CC(C)(C)OC(=O)Nc1cc(Oc2cccc(CCC(=O)Nc3cccc(C(C)(C)C)c3)c2)ccn1 | null | 85.4 | null |
72,374 | ord_dataset-520610070b3c4780a03b44c7fcecc28f | null | 1980-01-01T00:10:00 | true | [OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[O:5][C:4](=[O:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27]Cl)[CH2:21][CH2:20]1>>[O:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][O:1][C:2]2[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[O:5][C:... | ClCCCN1CCOCC1 | O=c1oc2c(c(O)c1-c1ccccc1)CCCC2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Obtained by causing the reaction, as indicated in Example 14, Stage B, of 14.5 g. (0.06 mol) of 4-hydroxy-3-phenyl-5,6,7,8-tetrahydrocoumarin with 15.6 g. (0.078 mol) of 3-morpholino-1-chloropropane. 10.1 g. of a paste which cannot be crystallised are isolated. Yield 45.7% (theoretical yield 22.1 g.). | O=c1oc2c(c(OCCCN3CCOCC3)c1-c1ccccc1)CCCC2 | null | 45.7 | null |
1,183,666 | ord_dataset-9cd817a75dfc4fe7ad19d4232772d5ff | null | 2012-01-01T00:07:00 | true | [O:1]1[C:5]2[CH2:6][NH:7][CH2:8][CH:9]([OH:10])[C:4]=2[CH:3]=[CH:2]1.F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([O:10][CH:9]2[CH2:8][NH:7][CH2:6][C:5]3[O:1][CH:2]=[CH:3][C:4]2=3)=[CH:13][CH:14]=1)#[N:17] | OC1CNCc2occc21 | N#Cc1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The same method as in Example 1 was conducted using 4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-ol (Reference Example 4) instead of 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-4-ol (Reference Example 6) and was conducted using 4-fluorobenzonitrile instead of 1-fluoronaphthalene to give the objective compound. | N#Cc1ccc(OC2CNCc3occc32)cc1 | null | null | null |
59,810 | ord_dataset-09e9a37ee5794dc28c0ad7bf7a442c18 | null | 1979-01-01T00:11:00 | true | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:16])([F:15])[CH2:13][OH:14].[OH-].[Li+].CS(C)=O>O>[F:11][C:12]([F:16])([F:15])[CH2:13][O:14][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1 | OCC(F)(F)F | O=[N+]([O-])c1ccc(Cl)nc1 | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | O | null | null | null | null | null | null | null | null | null | null | null | 2-Chloro-5-nitropyridine (9.5 grams), 2,2,2-trifluoroethanol (6.0 grams), and lithium hydroxide (4.0 grams) were mixed in 50 ml. of DMSO and stirred overnight (about 18 hours) at room temperature. The reaction mixture was then poured into water and the product was separated by filtration. It was crystallized from ethyl... | O=[N+]([O-])c1ccc(OCC(F)(F)F)nc1 | null | null | null |
1,377,161 | ord_dataset-d23f2f15886d4c22b7d7ba5f0e203e81 | null | 2013-01-01T00:12:00 | true | [NH2:1][C:2]1[C:7]([C:8]2[N:37]([C:38]3[CH:43]=[CH:42][C:41]([C:44]4([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])[CH2:47][CH2:46][CH2:45]4)=[CH:40][CH:39]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH2:27][CH2:26][O:25][C@H:24]([CH2:28][O:29]CC6C=CC=CC=6)[CH2:23]5)[CH:17]=4)=... | CC(C)(C)OC(=O)NC1(c2ccc(-n3c(-c4cccnc4N)nc4ccc(-c5cccc(N6CCO[C@H](COCc7ccccc7)C6)c5)nc43)cc2)CCC1 | 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 | 50 | 7.5 | 10% Pd/C (30 mg) was added to a solution of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-(3-{(2S)-2-[(benzyloxy)methyl]morpholin-4-yl}phenyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (36.0 mg, 0.0488 mmol) in MeOH (2 mL). The mixture was stirred at room temperature for 14 hours and 7.5 hours at 50° C. u... | CC(C)(C)OC(=O)NC1(c2ccc(-n3c(-c4cccnc4N)nc4ccc(-c5cccc(N6CCO[C@H](CO)C6)c5)nc43)cc2)CCC1 | null | 14.6 | null |
412,519 | ord_dataset-fbdd058349aa456f812e3546c84baab5 | null | 1998-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][CH2:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:34](Br)[CH:35]=[CH2:36].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:36... | O=C(O)c1ccc(CCCc2cc(O)ccc2OCc2ccccc2)cc1 | C=CCBr | 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 | O | null | null | null | null | null | null | null | null | null | null | 18 | To a mixture of 4-[3-(2-benzyloxy-5-hydroxyphenyl)propyl]- benzoic acid (150 mg) (prepared as described in Example 4) and potassium carbonate (125 mg) in DMF (5 ml) was added allyl bromide (0.076 ml). The mixture was stirred for 18 hours, then potassium carbonate (125 mg) and allyl bromide (0.076 ml) were added and the... | C=CCOc1ccc(OCc2ccccc2)c(CCCc2ccc(C(=O)O)cc2)c1 | null | null | null |
137,023 | ord_dataset-a1d4c9f5edd844798727d514977ca73e | null | 1985-01-01T00:11:00 | true | [F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].CO[C:21]1(OC)[CH2:25][CH2:24][CH2:23]O1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:21]=[CH:25][CH:24]=[CH:23]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16... | COC1(OC)CCCO1 | CCn1cc(C(=O)O)c(=O)c2cc(F)c(N)cc21 | 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 | 2.5 Grams of 6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are suspended in 15 ml of acetic acid, and 1.32 gram of dimethoxytetrahydrofuran is added; the mixture is heated gradually until the solid dissolves, and is then allowed to cool. The precipitate formed is filtered off and washed with eth... | CCn1cc(C(=O)O)c(=O)c2cc(F)c(-n3cccc3)cc21 | null | null | null |
688,472 | ord_dataset-56747de2718a4ac5bf061651d1cc9e3e | null | 2005-01-01T00:10:00 | true | [O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]3[C:18]4[C:17]5[CH:19]=[C:20]([NH:23][C:24]([C:26]6[C:27]([NH:32]CC7C=CC(OC)=CC=7)=[N:28][CH:29]=[CH:30][CH:31]=6)=[O:25])[CH:21]=[CH:22][C:16]=5[CH2:15][CH2:14][C:13]=4[C:12]([C:42]([NH2:44])=[O:43])=[N:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>C... | COc1ccc(CNc2ncccc2C(=O)Nc2ccc3c(c2)-c2c(c(C(N)=O)nn2-c2ccc4c(c2)OCO4)CC3)cc1 | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | The title compound of Example 209 (1.96 g, 0.0033 mol) was dissolved in 6 mL CH2Cl2 and reacted with 5 mL TFA at room temperature for 36 h. The crude reaction mixture was diluted with CH2Cl2 and basified with a saturated aqueous solution of Na2CO3. The layers were separated and the organic layer was dried over MgSO4. T... | NC(=O)c1nn(-c2ccc3c(c2)OCO3)c2c1CCc1ccc(NC(=O)c3cccnc3N)cc1-2 | null | 32.5 | null |
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