Trifluoroacetic acid → HCID 66715951, compound

HRID 2271805Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692950HCID 86692950, compound

Product 1

HCID 66715951HCID 66715951, compoundYield 55.3%

Procedure

Following general procedure A-2, tert-butyl 4-(4-((6-(3-chloro-4-hydroxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (27 mg, 55% over 2 steps) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.99 (s, 1H), 9.12 (s, 1H), 8.18 (d, J=2.2 Hz, 1H), 8.02-7.96 (m, 1H), 7.92-7.86 (m, 2H), 7.45 (d, J=2.3 Hz, 1H), 7.41 (s, 1H), 7.28-7.22 (m, 1H), 7.01 (d, J=8.5 Hz, 1H), 4.24-4.14 (m, 1H), 3.06-2.99 (m, 2H), 2.94-2.85 (m, 1H), 2.62-2.53 (m, 2H), 1.95-1.89 (m, 2H), 1.83-1.71 (m, 2H), 1.02-0.97 (m, 4H). ESI MS m/z 488 [C27H26ClN5O2+H]+; HPLC>99% (AUC), tR=9.30 min.

Sources & evidence

ORD record: ord-76363fc4d8584d429734d3c9b8f6750b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…