Trifluoroacetic acid → HCID 68091919, compound

HRID 2271744Notes

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]([CH:21]2[CH2:23][CH2:22]2)=[O:20])=[C:12]3[NH:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)[CH:5]=[CH:6][C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[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]([CH:21]2[CH2:23][CH2:22]2)=[O:20])=[C:12]3[NH:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692926HCID 86692926, compound

Product 1

HCID 68091919HCID 68091919, compoundYield 69.9%

Procedure

Following general procedure A-2, tert-butyl 4-{2-[6-(3-Chloro-4-hydroxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-ylamino]ethyl}piperazine-1-carboxylate (40 mg, 0.073 mmol) was reacted with TFA (2 mL) to afford the desired product (23 mg, 35%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.00 (s, 1H), 9.09 (s, 1H), 8.46 (d, J=1.8 Hz, 1H), 7.98 (dd, J=8.7, 1.9 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.78 (d, J=2.3 Hz, 1H), 7.61 (dd, J=8.5, 2.3 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 3.82 (d, J=5.2 Hz, 2H), 2.95-2.82 (m, 1H), 2.68 (t, J=4.7 Hz, 4H), 2.55 (t, J=6.0 Hz, 2H), 2.35 (s, 4H), 1.11-0.97 (m, 4H); ESI MS m/z 451 [C25H27ClN4O2+H]+; HPLC>99% (AUC), tR=9.32 min.

Sources & evidence

ORD record: ord-c8a63fc8d8424863b620edf1ae0c7be5
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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