Trifluoroacetic acid → HCID 58173380, compound

HRID 2047191Notes

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]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([C:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH:28]=2)[CH:9]=1.C(O)(C(F)(F)F)=O>>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:26]=[C:17]([C:16]2[CH:15]=[N:14][N:13]3[C:8]([NH2:7])=[CH:9][C:10]([C:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH:28]=4)=[N:11][C:12]=23)[CH:18]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67494206HCID 67494206, compound

Product 1

HCID 58173380HCID 58173380, compound

Procedure

tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.057 mmol, 40 mg) was charged to a 20 mL scintillation vial containing 1 mL TFA. The reaction mixture was stirred at room temperature. The reaction mixture was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield 3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (m+H=343.31, retention time=2.05 min)

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified via reverse-phase preparatory HPLC

Sources & evidence

ORD record: ord-b1c0337082954a78a4f6de1f9dcaea8a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591943B2

Reaction notes

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