Trifluoroacetic acid → HCID 178511270, compound

HRID 2271939Notes

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]([CH2:23][NH:24]C(=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>>[NH2:24][CH2:23][C@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:32]4[CH:37]=[C:36]([Cl:38])[C:35]([OH:39])=[C:34]([Cl:40])[CH:33]=4)[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH2:18][CH2:19]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178453637HCID 178453637, compound

Product 1

HCID 178511270HCID 178511270, compoundYield 40.3%

Procedure

Following general procedure A-2, tert-butyl {trans-4-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]cyclohexyl}methylcarbamate (0.123 mmol) was reacted with TFA (2 mL) to afford the desired product (24 mg, 40% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.36 (s, 1H), 8.47 (s, 1H), 8.27 (d, J=8.4 Hz, 1H), 7.98 (d, J=8.4 Hz, 1H), 7.74 (s, 2H), 4.54-4.48 (m, 1H), 2.92-2.76 (m, 3H), 2.50-2.37 (m, 2H), 2.08-2.02 (m, 2H), 1.83-1.64 (m, 3H), 1.41-1.15 (m, 6H); ESI MS m/z 484 [C26H27Cl2N3O2+H]+; HPLC>99% (AUC), tR=11.38 min.

Sources & evidence

ORD record: ord-bc5a8ac20ac64f8da669f73aa1de25c9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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