Trifluoroacetic acid → HCID 178509710, compound

HRID 416709Notes

Reaction equation

HRID 416709 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[NH:39][C:18]3=[N:19][CH:20]=[C:21]([Br:38])[C:22]([N:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:30](=[O:37])[NH:31][C:32]5[S:33][CH:34]=[CH:35][N:36]=5)[CH2:25][CH2:24]4)=[C:17]3[N:16]=2)[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]2[NH:39][C:18]3=[N:19][CH:20]=[C:21]([Br:38])[C:22]([N:23]4[CH2:24][CH2:25][N:26]([CH2:29][C:30]([NH:31][C:32]5[S:33][CH:34]=[CH:35][N:36]=5)=[O:37])[CH2:27][CH2:28]4)=[C:17]3[N:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 178453048HCID 178453048, compound

Product 1

HCID 178509710HCID 178509710, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-{6-Bromo-7-[4-(thiazol-2-ylcarbamoylmethyl)-piperazin-1-yl]-3H-imidazo[4,5-b]pyridin-2-yl}-benzyl)-carbamic acid tert-butyl ester (0.027 g, 0.04 mmol) in dichloromethane (5 mL) was slowly added trifluoroacetic acid (0.5 mL) at 0° C. trifluoroacetic acid (0.25 mL) was added and the reaction mixture was stirred for 1 h. The reaction mixture was stirred at room temperature for 1 h then concentrated in vacuo. The crude product was run trough a 2 g SCX cartridge and eluted with 0.1M NH3 in methanol to give the title compound as a pale yellow solid (0.023 g, 100%);

Workup

  1. customat 0° C.
  2. additionwas added
  3. stirringThe reaction mixture was stirred at room temperature for 1 h
  4. concentrationthen concentrated in vacuo
  5. washeluted with 0.1M NH3 in methanol

Sources & evidence

ORD record
ord-27c083d0437f4f92949b9e19568e6077
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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