Trifluoroacetic acid → HCID 178511644, compound

HRID 2271714Notes

Reaction equation

HRID 2271714 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][C:14]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])=[C:13]4[NH:25][C@H:26]3[CH2:31][CH2:30][C@H:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28][CH2:27]3)=[CH:9][C:4]=2[N:3]=[CH:2]1.C(O)(C(F)(F)F)=O>>[NH2:32][C@H:29]1[CH2:30][CH2:31][C@H:26]([NH:25][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:8]4[CH:7]=[CH:6][C:5]5[NH:1][CH:2]=[N:3][C:4]=5[CH:9]=4)[CH:11]=3)[N:16]=[CH:15][C:14]=2[C:20]([CH:22]2[CH2:23][CH2:24]2)=[O:21])[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454010HCID 178454010, compound

Product 1

HCID 178511644HCID 178511644, compoundYield 58.2%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(1H-benzo[d]imidazol-5-yl)-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexylcarbamate (45.3 mg, 0.086 mmol) was reacted with TFA (2 mL) to afford the desired product (21.3 mg, 58%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 9.16 (s, 1H), 8.48 (s, 1H), 8.27 (s, 1H), 8.12 (d, J=8.7 Hz, 1H), 7.99-7.93 (m, 2H), 7.74 (d, J=8.4 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 4.29 (s, 1H), 3.17 (s, 1H), 2.93-2.78 (m, 1H), 2.36 (d, J=11.1 Hz, 2H), 2.15 (d, J=11.2 Hz, 2H), 1.72-1.53 (m, 4H), 1.23-1.17 (m, 2H), 1.14-1.05 (m, 2H); ESI MS m/z 426 [C26H27N5O+H]+; HPLC 96.0% (AUC), tR=8.89 min.

Sources & evidence

ORD record
ord-a3b3fbb69b10480aa6635185f87f3d8a
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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