Trifluoroacetic acid → HCID 66716623, compound

HRID 2271800Notes

Reaction equation

[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:18]=[N:19][N:20]([CH:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)[CH:21]=2)=[CH:13][C:12]([C:35]2[CH:40]=[C:39]([Cl:41])[C:38]([OH:42])=[C:37]([Cl:43])[CH:36]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:18]=[N:19][N:20]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH:21]=2)=[CH:13][C:12]([C:35]2[CH:36]=[C:37]([Cl:43])[C:38]([OH:42])=[C:39]([Cl:41])[CH:40]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:2][CH2:3]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68092291HCID 68092291, compound

Product 1

HCID 66716623HCID 66716623, compoundYield 71%

Procedure

Following general procedure A-2, tert-butyl 4-(4-((3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (36 mg, 0.058 mmol) was reacted with TFA (2 mL) to afford the desired product (21.5 mg, 41%) as a yellow solid. 1H NMR (500 MHz, MeOD+TFA-d) δ 9.48 (br s, 1H), 8.22 (d, J=9.2 Hz, 1H), 8.01 (d, J=8.4 Hz, 2H), 7.69 (s, 1H), 7.39 (br s, 2H), 4.68-4.58 (m, 1H), 3.57 (dt, J=13.2, 3.8 Hz, 2H), 3.27-3.17 (m, 2H), 2.88 (br s, 1H), 2.36-2.25 (m, 4H), 1.41-1.10 (m, 4H). ESI MS m/z 522 [C27H25Cl2N5O2+H]+; HPLC>99% (AUC), tR=9.75 min.

Sources & evidence

ORD record: ord-80a0f959ddaf4c2e9ec34bc3d55df015
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…