Hydrogen Peroxide → 1-{[(1R,2R,4R)-4-Hydroxy-2-methylcyclohexyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1971011Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:21]3[C:20]4[CH:19]=[CH:18][C:17]([C:22]5[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=5)=[CH:16][C:15]=4[NH:14][C:13]=3[C:12]([C:28]#[N:29])=[CH:11][N:10]=2)[C@H:4]([CH3:30])[CH2:3]1.OO.C(=O)([O-])[O-:34].[K+].[K+]>CS(C)=O>[OH:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:21]3[C:20]4[CH:19]=[CH:18][C:17]([C:22]5[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=5)=[CH:16][C:15]=4[NH:14][C:13]=3[C:12]([C:28]([NH2:29])=[O:34])=[CH:11][N:10]=2)[C@H:4]([CH3:30])[CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-{[(1R,2R,4R)-4-hydroxy-2-methylcyclohexyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carbonitrile (15 mg, 0.037 mmol) in DMSO (2 mL) were added hydrogen peroxide (30%, 0.038 mL, 0.38 mmol) and potassium carbonate (28 mg, 0.20 mmol). The reaction mixture was heated to 70° C. overnight, cooled to room temperature, filtered, and purified by prep-HPLC to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 8.42 (s, 1H); 8.07 (d, 1H); 7.99 (s, 1H); 7.88 (s, 1H); 7.77 (s, 1H); 7.48 (dd, 1H); 3.97 (m, 1H); 3.93 (s, 3H); 3.69 (m, 1H); 1.22-2.17 (series of m, 7H); 1.03 (d, 3H). LRMS (APCI) calc'd for (C23H26N6O2) [M+H]+, 419.2. found 419.1.

Workup

temperaturecooled to room temperature
filtrationfiltered
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-5b459ce8689148409d26a0b4822ccc3c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431569B2

Reaction notes

Loading…