4-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol → 4-[4-(4-Bromo-benzyloxy)-2-(2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-ylamino)-phenylsulfanyl]-phenol

HRID 607267Notes

Reaction equation

HRID 607267 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]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=2)[CH:19]=[CH:18][C:17]=1[S:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1.NC1C=C(OCC2C=CC=C(Br)C=2)C=CC=1SC1C=CC(O)=CC=1>>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:20]2[CH:19]=[CH:18][C:17]([S:31][C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)=[C:16]([NH:2][C:1]3[C:3]4[S:7][C:6]([S:8][CH3:9])=[N:5][C:4]=4[N:10]=[CH:11][N:12]=3)[CH:21]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 668082684-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenolHCID 668082894-[2-Amino-4-(4-bromo-benzyloxy)-phenylsulfanyl]-phenol2×HCID 66808347N'-(5-Cyano-2-methylsulfanyl-thiazol-4-yl)-N,N-dimethyl-formamidine

Product 1

HCID 668084654-[4-(4-Bromo-benzyloxy)-2-(2-methylsulfanyl-thiazolo[4,5-d]pyrimidin-7-ylamino)-phenylsulfanyl]-phenolYield 27%

Procedure

A solution of the product from Example 167A and the product from Example 16A were reacted according to the procedure from Example 167B substituting the product from Example 16A for the product from Example 15A to provide the crude material which was purified by trituration with methanol to provide the title compound as a white solid (46 mg, 27%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 2.76 (s, 3H), 5.09 (s, 2H), 6.70 (d, J=8.46 Hz, 2H), 6.91-7.24 (m, 5H), 7.38 (d, J=8.09 Hz, 2H), 7.56 (d, J=8.09 Hz, 2H), 8.46 (s, 1H), 9.71 (s, 2H); MS (ESI)+ m/z 583/585 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-8ee15170f6fb4b46a998c0ecd9f56ee1
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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