Trifluoroacetic acid → HCID 178511649, compound

HRID 2271734Notes

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]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]2)=[CH:13][C:12]([C:31]2[CH:36]=[C:35]([F:37])[C:34]([OH:38])=[C:33]([F:39])[CH:32]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:23][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:31]4[CH:32]=[C:33]([F:39])[C:34]([OH:38])=[C:35]([F:37])[CH:36]=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 178454016HCID 178454016, compound

Product 1

HCID 178511649HCID 178511649, compoundYield 60.2%

Procedure

Following general procedure A-2, tert-butyl cis-4-[3-(cyclopropanecarbonyl)-6-(3,5-difluoro-4-hydroxyphenyl)quinolin-4-ylamino]cyclohexylcarbamate (51 mg, 0.095 mmol) was reacted with TFA (2 mL) to afford the desired product (25 mg, 52%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.27 (s, 1H), 8.37 (d, J=1.7 Hz, 1H), 8.06 (dd, J=8.8, 1.9 Hz, 1H), 7.94 (d, J=8.7 Hz, 1H), 7.33 (dd, J=8.1, 1.6 Hz, 2H), 4.73 (s, 1H), 2.97-2.86 (m, 1H), 2.16 (d, J=9.1 Hz, 2H), 2.09-1.97 (m, 5H), 1.91-1.76 (m, 2H), 1.27-1.20 (m, 2H), 1.20-1.10 (m, 2H); ESI MS m/z 438 [C25H25F2N3O2+H]+; HPLC>99% (AUC), tR=5.12 min.

Sources & evidence

ORD record: ord-b5b72480a2bf40a99112c73857cf900e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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