Pyridine → N-{4-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-methoxyphenyl}-4-methylbenzenesulfonamide

HRID 1181369Notes

Reaction equation

HRID 1181369 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:19](=[O:20])[C:18]3[S:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=4)=[CH:23][C:17]=3[N:16]=[CH:15]2)=[CH:10][C:9]=1[O:31][CH3:32].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>O>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[S:21][C:18]3[C:19](=[O:20])[N:14]([C:11]4[CH:12]=[CH:13][C:8]([NH:7][S:39]([C:36]5[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=5)(=[O:41])=[O:40])=[C:9]([O:31][CH3:32])[CH:10]=4)[CH:15]=[N:16][C:17]=3[CH:23]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 589808433-(4-Amino-3-methoxyphenyl)-6-(4-chlorophenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 58980855N-{4-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]-2-methoxyphenyl}-4-methylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A pyridine (1 mL) solution of 3-(4-Amino-3-methoxyphenyl)-6-(4-chloro-phenyl)thieno[3,2-d]pyrimidin-4(3H)-one (0.050 g, 0.0013 mol, the preparation of which is found in Example K13) and p-toluenesulfonyl chloride and was agitated overnight at RT, then diluted with water and filtered to give a white powder (0.056 g 81%). LCMS m/z 538 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 9.72 (s, 1H), 8.40 (s, 1H), 8.00 (s, 1H), 7.95 (d, 2H), 7.70 (d, 2H), 7.60 (d, 2H), 7.38 (d, 2H), 7.35 (d, 1H), 7.20 (s, 1H), 7.05 (d, 1H), 3.62 (s, 3H), 2.41 (s, 3H) ppm.

Workup

  1. filtrationfiltered
  2. customto give a white powder (0.056 g 81%)

Sources & evidence

ORD record
ord-2eebc6ab673e40638319a466ba28a94f
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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