N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide → N-{4-[4-Methyl-2-(2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 607268Notes

Reaction equation

HRID 607268 reaction equation
[C:1]([C:3]1[S:7][C:6]([S:8][CH3:9])=[N:5][C:4]=1[N:10]=[CH:11][N:12](C)C)#[N:2].N[C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=1.NC1C=C(OCC2C=CC=C(Br)C=2)C=CC=1SC1C=CC(O)=CC=1>>[CH3:22][C:20]1[CH:21]=[CH:16][C:17]([S:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:33])[CH3:32])=[CH:26][CH:25]=2)=[C:18]([NH:2][C:1]2[C:3]3[S:7][C:6]([S:8][CH3:9])=[N:5][C:4]=3[N:10]=[CH:11][N:12]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 43168935N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide2×HCID 668082684-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenolHCID 66808347N'-(5-Cyano-2-methylsulfanyl-thiazol-4-yl)-N,N-dimethyl-formamidine

Product 1

HCID 66808436N-{4-[4-Methyl-2-(2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-ylamino)-phenylsulfanyl]-phenyl}-acetamideYield 83%

Procedure

A solution of the product from Example 167A and the product from Example 7b were reacted according to the procedure from Example 167B substituting the product from Example 7b for the product from Example 15A to provide the crude material which was purified by trituration with methanol to provide the title compound (110 mg, 83%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.03 (s, 3H), 2.29 (s, 3H), 2.76 (s, 3H), 6.96 (d, J=8.09 Hz, 1H), 7.14 (d, J=8.09 Hz, 1H), 7.18-7.26 (m, J=8.82 Hz, 3H), 7.54 (d, J=8.46 Hz, 2H), 8.45 (s, 1H), 9.74 (s, 1H), 10.04 (s, 1H); MS (ESI)+ m/z 454 (M+H)+.

Workup

  1. customto provide the crude material which
  2. customwas purified by trituration with methanol

Sources & evidence

ORD record
ord-cb8a24e8f0d64d2a8312696fd8ac7319
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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