Trifluoroacetic acid → HCID 178450291, compound

HRID 2271763Notes

Reaction equation

HRID 2271763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][C:14]([C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:13]3[NH:25][C@H:26]2[CH2:31][CH2:30][C@H:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28][CH2:27]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[NH2:32][C@H:29]1[CH2:30][CH2:31][C@H:26]([NH:25][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:4]4[CH:3]=[C:2]([F:1])[C:7]([OH:8])=[C:6]([F:9])[CH:5]=4)[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178450292HCID 178450292, compound

Product 1

HCID 178450291HCID 178450291, compoundYield 36%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(3,5-difluoro-4-hydroxyphenyl)-3-isobutyrylquinolin-4-ylamino]cyclohexylcarbamate (64 mg, 0.100 mmol) was reacted with TFA (2 mL) to afford the desired product (10.8 mg, 36%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.97 (s, 1H), 8.32 (d, J=1.8 Hz, 1H), 8.00 (dd, J=8.7, 2.0 Hz, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.28 (dd, J=7.8, 1.9 Hz, 2H), 4.26-4.15 (m, 1H), 3.81-3.69 (m, 1H), 3.27-3.18 (m, 1H), 2.38 (d, J=12.6 Hz, 2H), 2.18 (d, J=11.7 Hz, 2H), 1.69 (q, J=10.4 Hz, 2H), 1.61-1.53 (m, 2H), 1.24 (d, J=6.8 Hz, 6H); ESI MS m/s 440 [C25H27F2N3O2+H]+; HPLC 95.0% (AUC), tR=10.50 min.

Sources & evidence

ORD record
ord-203f7ef006104defb70df770f42cfd77
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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