Trifluoroacetic acid → HCID 178484826, compound

HRID 2271942Notes

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@H:17]2[CH2:22][CH2:21][C@H:20]([N:23](C)[C:24](=O)OC(C)(C)C)[CH2:19][CH2:18]2)=[CH:13][C:12]([C:32]2[CH:37]=[C:36]([Cl:38])[C:35]([OH:39])=[C:34]([Cl:40])[CH:33]=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@H:17]2[CH2:18][CH2:19][C@H:20]([NH:23][CH3:24])[CH2:21][CH2:22]2)=[CH:13][C:12]([C:32]2[CH:37]=[C:36]([Cl:38])[C:35]([OH:39])=[C:34]([Cl:40])[CH:33]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178486049HCID 178486049, compound

Product 1

HCID 178484826HCID 178484826, compoundYield 51.6%

Procedure

Following general procedure A-2, tert-butyl trans-4-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]cyclohexyl(methyl)carbamate (0.120 mmol) was reacted with TFA (2 mL) to afford the desired product (30 mg, 51% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.35 (s, 1H), 8.48 (s, 1H), 8.28 (d, J=8.7 Hz, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.75 (s, 2H), 4.52 (s, 1H), 2.84 (s, 1H), 2.73 (s, 2H), 2.53-2.46 (m, 2H), 2.38-2.28 (m, 2H), 1.88-1.77 (m, 2H), 1.65-1.58 (m, 2H), 1.33-1.20 (m, 4H); ESI MS m/z 484 [C26H27Cl2N3O2+H]+; HPLC>99% (AUC), tR=9.66 min.

Sources & evidence

ORD record: ord-7e0256674e024000b7ae8694e4d1c87a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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