Trifluoroacetic acid → HCID 66715213, compound

HRID 2271947Notes

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:22]=[CH:21][C:20]([C:23]([NH:26]C(=O)OC(C)(C)C)([CH3:25])[CH3:24])=[CH:19][CH:18]=2)=[CH:13][C:12]([C:34]2[CH:39]=[C:38]([Cl:40])[C:37]([OH:41])=[C:36]([Cl:42])[CH:35]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:26][C:23]([C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:34]4[CH:35]=[C:36]([Cl:42])[C:37]([OH:41])=[C:38]([Cl:40])[CH:39]=4)[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])=[CH:22][CH:21]=1)([CH3:25])[CH3:24]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692988HCID 86692988, compound

Product 1

HCID 66715213HCID 66715213, compoundYield 28.6%

Procedure

Following general procedure A-2, tert-butyl 2-{4-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]phenyl}propan-2-ylcarbamate (0.145 mmol) was TFA (2 mL) to afford the desired product (21 mg, 28% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.33 (s, 1H), 8.26 (dd, J=8.8, 1.9 Hz, 1H), 8.19 (s, 1H), 8.05 (d, J=8.8 Hz, 1H), 7.67 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H), 7.43 (s, 2H), 2.82-2.73 (m, 1H), 1.78 (s, 6H), 1.18-1.10 (m, 4H); ESI MS m/z 506 [C28H25Cl2N3O2+H]+; HPLC 98.7% (AUC), tR=11.00 min.

Sources & evidence

ORD record: ord-8dc35dd076164274b3312866cf808d30
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

Loading…