Trifluoroacetic acid → HCID 178448148, compound

HRID 539037Notes

Reaction equation

[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[CH2:13][C@H:12]([CH:14]([CH3:16])[CH3:15])[N:11]([C:17]3[CH:22]=[CH:21][N:20]4[N:23]=[CH:24][C:25]([C:26]5[CH:31]=[CH:30][C:29]([C:32]6[N:36]=[CH:35][N:34](COCC[Si](C)(C)C)[N:33]=6)=[CH:28][CH:27]=5)=[C:19]4[N:18]=3)[C:10]2=[O:45])[CH2:3]1.FC(F)(F)C(O)=O>>[NH:34]1[CH:35]=[N:36][C:32]([C:29]2[CH:30]=[CH:31][C:26]([C:25]3[CH:24]=[N:23][N:20]4[CH:21]=[CH:22][C:17]([N:11]5[C@@H:12]([CH:14]([CH3:15])[CH3:16])[CH2:13][N:9]([CH2:8][CH2:7][N:4]6[CH2:5][CH2:6][C@@H:2]([F:1])[CH2:3]6)[C:10]5=[O:45])=[N:18][C:19]=34)=[CH:27][CH:28]=2)=[N:33]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid2×

HCID 67034711(S)-1-(2-((R)-3-fluoropyrrolidin-1-yl)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

Product 1

HCID 178448148HCID 178448148, compoundYield 72.1%

Procedure

To (S)-1-(2-((R)-3-fluoropyrrolidin-1-yl)ethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.025 g, 0.0394 mmol) was added trifluoroacetic acid (5 mL) and the reaction stirred for 2 hours at ambient temperature. The reaction was concentrated in vacuo and the material purified by reverse preparative HPLC to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-((R)-3-fluoropyrrolidin-1-yl)ethyl)-4-isopropylimidazolidin-2-one (0.0143 g, 0.0284 mmol, 72.0% yield) as the bis TFA salt. LCMS (APCI+) m/z 504 [M+H]+.

Workup

concentrationThe reaction was concentrated in vacuo
customthe material purified by reverse preparative HPLC

Sources & evidence

ORD record: ord-30c2c80394824eb7b6b905e0c74a2547
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

Loading…