Trifluoroacetic acid → HCID 178450277, compound

HRID 2271765Notes

Reaction equation

[Cl: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]([Cl: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]([Cl:1])[C:7]([OH:8])=[C:6]([Cl: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

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178450280HCID 178450280, compound

Product 1

HCID 178450277HCID 178450277, compoundYield 43%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(3,5-dichloro-4-hydroxyphenyl)-3-isobutyrylquinolin-4-ylamino]cyclohexylcarbamate (60 mg, 0.100 mmol) was reacted with TFA (2 mL) to afford the desired product (20.3 mg, 43%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 8.98 (s, 1H), 8.33 (s, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.67 (s, 2H), 4.18 (s, 1H), 3.80-3.70 (m, 1H), 2.96 (s, 1H), 2.40 (d, J=11.4 Hz, 2H), 2.20 (d, J=12.2 Hz, 2H), 1.73 (q, J=11.1 Hz, 2H), 1.65-1.53 (m, 2H), 1.24 (d, J=6.8 Hz, 6H); ESI MS m/z 472 [C25H27Cl2N3O2+H]+; HPLC 98.7% (AUC), tR=10.95 min.

Sources & evidence

ORD record: ord-acd8062a9298438ea7f7fc88b971e06d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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