Trifluoroacetic acid → HCID 178509552, compound

HRID 2271715Notes

Reaction equation

HRID 2271715 reaction equation
[C:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[CH:13][C:12]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])=[C:11]3[NH:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([NH:30]C(=O)OC(C)(C)C)[CH2:26][CH2:25]2)=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>>[NH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([NH:23][C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:6]4[S:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=4)[CH:9]=3)[N:14]=[CH:13][C:12]=2[C:18]([CH:20]2[CH2:21][CH2:22]2)=[O:19])[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454011HCID 178454011, compound

Product 1

HCID 178509552HCID 178509552, compoundYield 67.4%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(5-cyanothiophen-2-yl)-3-(cyclopropane carbonyl)quinolin-4-ylamino]cyclohexylcarbamate (24 mg, 0.047 mmol) was reacted with TFA (2 mL) to afford the desired product (13.2 mg, 32%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.25 (s, 1H), 8.54 (s, 1H), 8.27 (d, J=8.6 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.85 (d, J=4.0 Hz, 1H), 7.70 (d, J=4.0 Hz, 1H), 4.28 (s, 1H), 3.28-3.25 (m, 1H), 2.89-2.83 (m, 1H), 2.42 (d, J=12.8 Hz, 2H), 2.23 (d, J=12.2 Hz, 2H), 1.80-1.63 (m, 4H), 1.27-1.21 (m, 2H), 1.19-1.13 (m, 2H); ESI MS m/z 417 [C24H24N4OS+H]+; HPLC 95.1% (AUC), tR=10.32 min.

Sources & evidence

ORD record
ord-2d0c4a0788a045c3af1de02b4b471468
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…