Hydrochloric Acid → HCID 178450274, compound

HRID 2271761Notes

Reaction equation

HRID 2271761 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](=[O:23])[CH:20]([CH3:22])[CH3:21])=[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][CH:4]=1)#[N:2].Cl>>[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:5]=[CH:4][C:3]([C:1]#[N:2])=[N:8][CH:7]=4)[CH:10]=3)[N:15]=[CH:14][C:13]=2[C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 178450275HCID 178450275, compound

Product 1

HCID 178450274HCID 178450274, compoundYield 54.1%

Procedure

Following general procedure A-1, tert-butyl trans-4-[6-(6-cyanopyridin-3-yl)-3-isobutyrylquinolin-4-ylamino]cyclohexylcarbamate (47.7 mg, 0.093 mmol) was reacted with 6 N hydrochloric acid (3 mL) to afford the desired product (20.8 mg, 54%) as a light yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.13-9.11 (m, 1H), 9.06 (s, 1H), 8.55 (d, J=1.8 Hz, 1H), 8.39 (dd, J=8.1, 2.3 Hz, 1H), 8.19 (dd, J=8.7, 1.9 Hz, 1H), 8.04 (d, J=3.8 Hz, 1H), 8.02 (d, J=4.4 Hz, 1H), 4.35-4.27 (m, 1H), 3.82-3.73 (m, 1H), 3.29-3.22 (m, 1H), 2.40 (d, J=12.7 Hz, 2H), 2.19 (d, J=12.1 Hz, 2H), 1.78-1.68 (m, 2H), 1.67-1.56 (m, 2H), 1.25 (d, J=6.8 Hz, 6H); ESI MS m/z 414 [C25H27N5O+H]+; HPLC 98.3% (AUC), tR=7.96 min.

Sources & evidence

ORD record
ord-479eb991a0c14cd1ac196d855a7adf23
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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