Trifluoroacetic acid → HCID 178467084, compound

HRID 2271772Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]1)=[CH:11][C:10]([C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([OH:36])=[C:31]([Cl:37])[CH:30]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[NH2:21][C@H:18]1[CH2:19][CH2:20][C@H:15]([NH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:29]4[CH:30]=[C:31]([Cl:37])[C:32]([OH:36])=[C:33]([Cl:35])[CH:34]=4)[CH:11]=3)[N:6]=[CH:5][C:4]=2[C:1](=[O:3])[CH3:2])[CH2:16][CH2:17]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178467087HCID 178467087, compound

Product 1

HCID 178467084HCID 178467084, compoundYield 51.4%

Procedure

Following general procedure A-2, tert-butyl trans-4-[3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]cyclohexylcarbamate (46 mg, 0.085 mmol) was reacted with TFA (2 mL) to afford the desired product (19.4 mg, 51%) as an orange solid: 1H NMR (500 MHz, DMSO-d6+D2O) δ 8.92 (s, 1H), 8.20 (s, 1H), 8.04 (d, J=8.9 Hz, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.63 (s, 2H), 4.09 (s, 1H), 3.20-3.11 (m, 1H), 2.68 (s, 3H), 2.26 (d, J=12.7 Hz, 2H), 2.08 (d, J=10.1 Hz, 2H), 1.69-1.58 (m, 2H), 1.57-1.46 (m, 2H); ESI MS m/z 444 [C23H23Cl2N3O2+H]+; HPLC>99% (AUC), tR=8.70 min.

Sources & evidence

ORD record: ord-e5aee95d9ceb4d869520d5a605adfbb8
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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