Trifluoroacetic acid → HCID 178511652, compound

HRID 2271722Notes

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@H:17]2[CH2:22][CH2:21][C@H:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]2)=[CH:13][C:12]([C:31]2[CH:32]=[N:33][NH:34][CH:35]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:23][C@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:31]4[CH:32]=[N:33][NH:34][CH:35]=4)[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH2:18][CH2:19]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178454020HCID 178454020, compound

Product 1

HCID 178511652HCID 178511652, compoundYield 45.1%

Procedure

Following general procedure A-2, tert-butyl trans-4-[3-(cyclopropanecarbonyl)-6-(1H-pyrazol-4-yl)quinolin-4-ylamino]cyclohexylcarbamate (17 mg, 0.036 mmol) was reacted with TFA (2 mL) to afford the desired product (6.1 mg, 45%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.30 (br s, 1H), 8.54 (br s, 1H), 8.29 (dd, J=8.7, 1.7 Hz, 1H), 8.19 (s, 2H), 7.94 (d, J=8.8 Hz, 1H), 2.84 (s, 1H), 2.44 (s, 2H), 2.24 (d, J=11.1 Hz, 2H), 1.89-1.76 (m, 2H), 1.67 (br s, 2H), 1.35-1.19 (m, 6H); ESI MS m/z 376 [C22H25N5O+H]+; HPLC 97.6% (AUC), tR=9.39 min.

Sources & evidence

ORD record: ord-8165473c927a469eb7c74bcbffb3bcae
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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