Trifluoroacetic acid → HCID 66715231, compound

HRID 2271945Notes

Reaction equation

[CH:1]1([C:4]([C:6]2[CH:7]=[N:8][C:9]3[C:14]([C:15]=2[NH:16][C:17]2[CH:31]=[CH:30][C:20]([CH2:21][NH:22]C(=O)OC(C)(C)C)=[CH:19][CH:18]=2)=[CH:13][C:12]([C:32]2[CH:37]=[C:36]([Cl:38])[C:35]([OH:39])=[C:34]([Cl:40])[CH:33]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:22][CH2:21][C:20]1[CH:30]=[CH:31][C:17]([NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:32]4[CH:33]=[C:34]([Cl:40])[C:35]([OH:39])=[C:36]([Cl:38])[CH:37]=4)[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:18][CH:19]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68091974HCID 68091974, compound

Product 1

HCID 66715231HCID 66715231, compoundYield 46.5%

Procedure

Following general procedure A-2, tert-butyl 4-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]benzylcarbamate (0.117 mmol) was reacted with TFA (2 mL) to afford the desired product (26 mg, 46% over two steps) a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.44 (s, 1H), 8.25 (d, J=8.7 Hz, 1H), 8.09-7.95 (m, 2H), 7.70 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.24 (s, 2H), 4.28 (s, 2H), 2.88-2.83 (m, 1H), 1.26-1.13 (m, 4H); ESI MS m/z 478 [C26H21Cl2N3O2+H]+; HPLC>99% (AUC), tR=11.99 min.

Sources & evidence

ORD record: ord-3d375bd4442b43fcae60b65fabad0d7c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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