Trifluoroacetic acid → HCID 67494339, compound

HRID 2047175Notes

Reaction equation

HRID 2047175 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([O:29][CH:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)[C:9]=1[C:43]([O:45]CC)=[CH2:44].C(O)(C(F)(F)F)=O>O>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([O:29][CH:30]2[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]2)[C:9]=1[C:43](=[O:45])[CH3:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66745622HCID 66745622, compound

Product 1

HCID 67494339HCID 67494339, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The crude tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)piperidine-1-carboxylate was treated with 50% TFA in H2O (6 mL) and stirred overnight. The reaction mixture was concentrated in vacuo. Purification with prep-LC provided 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yloxy)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone: LCMS tR=1.11 Min (5 min run, UV254nm). Mass calculated for, M+ 428.1, observed LC/MS m/z 429.1 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-46a3006aa911453d9aa8e012f1c41dc4
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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