Trifluoroacetic acid → HCID 66715244, compound

HRID 2271944Notes

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]([CH:22]2[CH2:24][CH2:23]2)=[O:21])=[C:13]3[NH:25][C:26]2[CH:40]=[CH:39][C:29]([CH2:30][NH:31]C(=O)OC(C)(C)C)=[CH:28][CH:27]=2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].C(O)(C(F)(F)F)=O>>[NH2:31][CH2:30][C:29]1[CH:39]=[CH:40][C:26]([NH:25][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:4]4[CH:5]=[C:6]([F:9])[C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=4)[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68092237HCID 68092237, compound

Product 1

HCID 66715244HCID 66715244, compoundYield 53%

Procedure

Following general procedure A-2, tert-butyl 4-[6-(3-chloro-5-fluoro-4-hydroxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-ylamino]benzylcarbamate (0.127 mmol) was reacted with TFA (2 mL) to afford the desired product (31 mg, 53% over two steps) as a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.44 (s, 1H), 8.24 (dd, J=8.9, 1.9 Hz, 1H), 8.08-7.96 (m, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.17-7.06 (m, 1H), 7.06-6.98 (m, 1H), 4.27 (s, 2H), 2.93-2.80 (m, 1H), 1.25-1.11 (m, 4H); ESI MS m/z 462 [C26H21ClFN3O2+H]+; HPLC>99% (AUC), tR=12.22 min.

Sources & evidence

ORD record: ord-c5daf4ad257f41c2b1a4fb159784fde4
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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