Trifluoroacetic acid → N-(azetidin-3-yl)-2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamide

HRID 1896964Notes

Reaction equation

[F:1][C:2]([F:33])([C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][N:13]=[C:14]2[NH:17][CH2:18][C:19]([NH:21][CH:22]2[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]2)=[O:20])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].C(O)(C(F)(F)F)=O>ClCCl>[NH:24]1[CH2:25][CH:22]([NH:21][C:19](=[O:20])[CH2:18][NH:17][C:14]2[C:15]3[C:10](=[CH:9][CH:8]=[C:7]([C:2]([F:1])([F:33])[C:3]([F:6])([F:4])[F:5])[CH:16]=3)[CH:11]=[CH:12][N:13]=2)[CH2:23]1

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 8 mL sealed tube, was placed a solution of tert-butyl 3-(2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamido)azetidine-1-carboxylate (as prepared in the previous step, 100 mg, 0.21 mmol, 1.00 equiv) in dichloromethane (5 mL), TFA (0.5 g). The resulting solution was stirred for 5 h at 0° C. The resulting mixture was concentrated under vacuum. The residue was washed with 3×5 mL of ether. This resulted in 0.12 g (crude) of N-(azetidin-3-yl)-2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamide as a white solid.

Workup

customInto a 8 mL sealed tube
concentrationThe resulting mixture was concentrated under vacuum
washThe residue was washed with 3×5 mL of ether
customThis resulted in 0.12 g (crude) of N-(azetidin-3-yl)-2-[[7-(pentafluoroethyl)isoquinolin-1-yl]amino]acetamide as a white solid

Sources & evidence

ORD record: ord-b5202008192e4dc4bccf619659212041
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

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