Trifluoroacetic acid → HCID 178510573, compound

HRID 2271713Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178454019HCID 178454019, compound

Product 1

HCID 178510573HCID 178510573, compoundYield 33.2%

Procedure

Following general procedure A-2, tert-butyl trans-4-[6-(2-cyanopyrimidin-5-yl)-3-(cyclopropane carbonyl)quinolin-4-ylamino]cyclohexylcarbamate (52 mg, 0.100 mmol) was reacted with TFA (1 mL) to afford the desired product (13.7 mg, 33%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.33 (s, 2H), 9.19 (s, 1H), 8.60 (d, J=1.9 Hz, 1H), 8.20 (dd, J=8.7, 2.0 Hz, 1H), 8.05 (d, J=8.7 Hz, 1H), 4.25-4.16 (m, 1H), 3.15-3.07 (m, 1H), 2.90-2.81 (m, 1H), 2.34 (d, J=13.1 Hz, 2H), 2.12 (d, J=11.8 Hz, 2H), 1.69-1.59 (m, 2H), 1.55-1.45 (m, 2H), 1.24-1.19 (m, 2H), 1.15-1.10 (m, 2H); ESI MS m/z 413 [C24H24N6O+H]+; HPLC 94.9% (AUC), tR=9.67 min.

Sources & evidence

ORD record: ord-1bbeb464c8624ebbb4b5a24136ba71bf
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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