Trifluoroacetic acid → HCID 178487410, compound

HRID 2271940Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178487411HCID 178487411, compound

Product 1

HCID 178487410HCID 178487410, compoundYield 47.4%

Procedure

Following general procedure A-2, tert-butyl {trans-4-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexyl}methylcarbamate (0.123 mmol) was reacted with TFA (2 mL) to afford the desired product (28 mg, 47% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.35 (s, 1H), 8.49 (s, 1H), 8.30 (d, J=8.7 Hz, 1H), 7.97 (d, J=8.7 Hz, 1H), 7.33 (s, 1H), 7.26 (s, 1H), 4.0 (s, 1H), 3.99 (s, 3H), 2.90-2.81 (m, 3H), 2.47-2.41 (m, 2H), 2.10-1.98 (m, 2H), 1.83-1.64 (m, 3H), 1.37-1.17 (m, 6H); ESI MS m/z 480 [C27H30ClN3O3+H]+; HPLC>99% (AUC), tR=11.15 min.

Sources & evidence

ORD record: ord-c5ee80cd059c4533a0a4c9a5570feba3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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