Trifluoroacetic acid → HCID 178487421, compound

HRID 2271802Notes

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](=[O:25])[CH:22]([CH3:24])[CH3:23])=[C:14]3[NH:26][C@H:27]2[CH2:32][CH2:31][C@H:30]([NH:33]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>>[NH2:33][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](=[O:25])[CH:22]([CH3:23])[CH3:24])[CH2:28][CH2:29]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178487422HCID 178487422, compound

Product 1

HCID 178487421HCID 178487421, compoundYield 35.5%

Procedure

Following general procedure A-2, tert-butyl (trans-4-((6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-isobutyrylquinolin-4-yl)amino)cyclohexyl)carbamate (0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (16.6 mg, 35% over 2 steps) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 8.96 (s, 1H), 8.34 (d, J=2.1 Hz, 2H), 8.03 (dd, J=8.6, 2.1 Hz, 1H), 7.90 (d, J=8.6 Hz, 1H), 7.28 (d, J=2.2 Hz, 1H), 7.20 (d, J=2.2 Hz, 1H), 4.22-4.13 (m, 1H), 3.98 (s, 3H), 3.81-3.71 (m, 2H), 3.03-2.94 (m, 1H), 2.38-2.32 (d, J=12.6 Hz, 2H), 2.13-2.06 (m, 2H), 1.73-1.61 (q, J=12.5 Hz, 2H), 1.50-1.38 (m, 2H), 1.24 (d, J=6.7 Hz, 6H). ESI MS m/z 468 [C26H30ClN3O3+H]+; HPLC>99% (AUC), tR=11.34 min.

Sources & evidence

ORD record: ord-38dbdb0129a54e8595af4c2eee4133d0
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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