Trifluoroacetic acid → HCID 178450284, compound

HRID 2271764Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178450285HCID 178450285, compound

Product 1

HCID 178450284HCID 178450284, compoundYield 48.8%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(3-chloro-4-hydroxyphenyl)-3-isobutyrylquinolin-4-ylamino]cyclohexylcarbamate (39 mg, 0.072 mmol) was reacted with TFA (2 mL) to afford the desired product (15.4 mg, 41%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.05 (s, 1H), 8.40 (s, 1H), 8.13 (d, J=8.8 Hz, 1H), 7.95 (d, J=8.7 Hz, 1H), 7.72 (d, J=2.3 Hz, 1H), 7.54 (dd, J=8.4, 2.3 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 4.31 (s, 1H), 3.80-3.72 (m, 1H), 3.29-3.26 (m, 1H), 2.44 (d, J=12.7 Hz, 2H), 2.22 (d, J=10.6 Hz, 2H), 1.84-1.74 (m, 2H), 1.67-1.56 (m, 2H), 1.25 (d, J=6.8 Hz, 6H); ESI MS m/z 438 [C25H28ClN3O2+H]+; HPLC 96.5% (AUC), tR=9.19 min.

Sources & evidence

ORD record: ord-29fb2a78f38f4d1c96a08cba80b4d538
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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