Trifluoroacetic acid methylene chloride → N-(3-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-aminoacetamide

HRID 2262064Notes

Reaction equation

HRID 2262064 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:41])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[S:25][C:24]3[C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[N:22][C:21]([C:32]4[CH:40]=[CH:39][CH:38]=[C:37]5[C:33]=4[CH:34]=[N:35][NH:36]5)=[N:20][C:19]=3[CH:18]=2)[CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>>[NH:36]1[C:37]2[C:33](=[C:32]([C:21]3[N:22]=[C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[C:24]4[S:25][C:17]([C:13]5[CH:12]=[C:11]([NH:10][C:9](=[O:41])[CH2:8][NH2:7])[CH:16]=[CH:15][CH:14]=5)=[CH:18][C:19]=4[N:20]=3)[CH:40]=[CH:39][CH:38]=2)[CH:34]=[N:35]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131728571HCID 131728571, compound

Product 1

HCID 59592994N-(3-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)-2-aminoacetamideYield 20.4%

Procedure

Tert-butyl(3-(2-(1H-indazol-4-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylcarbamoyl)methylcarbamate (82 mg) was treated with 2 mL of trifluoroacetic acid/dichloromethane (1:1). Upon completion, the reaction mixture was evaporated. The product was purified by reverse phase HPLC to yield 13.9 mg of 137. MS (Q1) 486 (M)+.

Workup

  1. customUpon completion, the reaction mixture was evaporated
  2. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a4f3451d3783492a958a4bcbb2dc41b0
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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