Trifluoroacetic acid → HCID 178487372, compound

HRID 2271781Notes

Reaction equation

HRID 2271781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][C:20]=2[F:21])[N:17]=[CH:16][C:15]([C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])=[C:14]3[NH:27][C@H:28]2[CH2:33][CH2:32][C@H:31]([NH:34]C(=O)OC(C)(C)C)[CH2:30][CH2:29]2)[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[NH2:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([NH:27][C:14]2[C:13]3[C:18](=[CH:19][C:20]([F:21])=[C:11]([C:4]4[CH:5]=[C:6]([O:9][CH3:10])[C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=4)[CH:12]=3)[N:17]=[CH:16][C:15]=2[C:22]([CH:24]2[CH2:25][CH2:26]2)=[O:23])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487373HCID 178487373, compound

Product 1

HCID 178487372HCID 178487372, compoundYield 68.1%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)-7-fluoroquinolin-4-ylamino]cyclohexylcarbamate (53 mg, 0.091 mmol) was reacted with TFA (2 mL) to afford the desired product (30 mg, 48%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.23 (s, 1H), 8.35 (d, J=7.8 Hz, 1H), 7.65 (d, J=11.2 Hz, 1H), 7.21 (d, J=10.6 Hz, 2H), 4.20 (s, 1H), 3.95 (s, 3H), 2.84 (s, 1H), 2.39 (d, J=12.4 Hz, 2H), 2.18 (d, J=11.5 Hz, 2H), 1.83-1.64 (m, 2H), 1.62-1.43 (m, 2H), 1.31-1.09 (m, 4H); ESI MS m/z 484 [C26H27ClFN3O3+H]+; HPLC 98.1% (AUC), tR=8.84 min.

Sources & evidence

ORD record
ord-5225bf65d1f849a88846fc9a3ca7941a
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…