Hexane ethanol diethylamine → HCID 117769866, compound

HRID 1526368Notes

Reaction equation

HRID 1526368 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:28])[N:8]([CH:23]([CH:25]([CH3:27])[CH3:26])[CH3:24])[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:13][N:12]=3)[C:5]=2[NH:4][N:3]=1.CCCCCC.C(O)C.C(NCC)C>>[NH2:1][C:2]1[C:6]2[C:7](=[O:28])[N:8]([C@H:23]([CH:25]([CH3:27])[CH3:26])[CH3:24])[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)=[CH:13][N:12]=3)[C:5]=2[NH:4][N:3]=1

Participants

3

Reactant 2

HCID 21881120Hexane ethanol diethylamineHCID 117770482HCID 117770482, compound

Product 1

HCID 117769866HCID 117769866, compoundYield 44.4%

Procedure

Racemic 3-amino-5-(3-methylbutan-2-yl)-7-(5-(morpholin-4-yl)pyridin-2-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Example 116 (90 mg) was resolved by HPLC (column: CHIRALCEL OJ, 50 mmID×500 mmL, manufactured by Daicel Chemical Industries, mobile phase: hexane/ethanol/diethylamine=700/300/1(v/v/v)) to give the title compound (40 mg) having a longer retention time. 99.2% ee (HPLC (column: CHIRALCEL OJ3, 4.6 mmID×250 mmL, manufactured by Daicel Chemical Industries, mobile phase: hexane/ethanol/diethylamine=700/300/1(v/v/v), flow rate: 1.0 mL/min, retention time: 16.41 min))

Sources & evidence

ORD record
ord-6897e233863c477bbc9408f48e46dfcf
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…