Trifluoroacetic acid → Trifluoroacetic acid

HRID 2368981Notes

Reaction equation

HRID 2368981 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].C[Si](C)(C)CCOC[N:14]([CH2:54]OCC[Si](C)(C)C)[C:15]1[N:20]2[N:21]=[CH:22][C:23]([C:24]3[CH:25]=[N:26][C:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:28][CH:29]=3)=[C:19]2[N:18]=[C:17]([CH:36]2[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]2)[C:16]=1[C:49]([O:51]CC)=[CH2:50]>>[C:30]1([C:27]2[N:26]=[CH:25][C:24]([C:23]3[CH:22]=[N:21][N:20]4[C:15]5[NH:14][CH2:54][CH2:50][C:49](=[O:51])[C:16]=5[C:17]([CH:36]5[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]5)=[N:18][C:19]=34)=[CH:29][CH:28]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1.[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66584806Tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 1361688203-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one

Procedure

At 0° C., TFA (5 mL) was added to tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(1-ethoxyvinyl)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate. The mixture was stirred for 1 h at room temperature. Concentration afforded 3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)-8,9-dihydropyrazolo[1,5-a]pyrido[3,2-e]pyrimidin-6(7H)-one as an TFA salt. LCMS tR=0.99 Min (5 min run, UV254nm). Mass calculated for, M+ 424.2, observed LC/MS m/z 425.2 (M+H).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-a117f457357948bd838a4ca83e04e1a1
Source dataset
uspto-grants-2014_04
Patent number
US08703784B2

Reaction notes

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