HCID 70979181, compound → HCID 70979810, compound

HRID 1485447Notes

Reaction equation

HRID 1485447 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:17]4[C:18]([CH3:21])=[N:19][N:20]=[C:16]4[CH:15]([CH3:22])[CH2:14][N:13]([C:23]4[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=4)[C:12]=3[CH:32]=2)=[CH:4][CH:3]=1>CCCCCC.C(O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:17]4[C:18]([CH3:21])=[N:19][N:20]=[C:16]4[C@H:15]([CH3:22])[CH2:14][N:13]([C:23]4[CH:24]=[CH:25][C:26]([C:27]([NH2:29])=[O:28])=[CH:30][CH:31]=4)[C:12]=3[CH:32]=2)=[CH:4][CH:3]=1.[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:17]4[C:18]([CH3:21])=[N:19][N:20]=[C:16]4[C@@H:15]([CH3:22])[CH2:14][N:13]([C:23]4[CH:24]=[CH:25][C:26]([C:27]([NH2:29])=[O:28])=[CH:30][CH:31]=4)[C:12]=3[CH:32]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70979181HCID 70979181, compound

Product 2

HCID 70979460HCID 70979460, compoundYield 47.5%HCID 70979810HCID 70979810, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzamide (80 mg, 0.19 mmol) was separated by chiral HPLC (Daicel AD-H (250 mm×20 mm×5 μm), hexane/ethanol (0.2 diethylamine)=30:70, flow rate: 13 mL/min), then (R)-4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzamide (27 mg, 67.5%) and (S)-4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzamide (19 mg, 47.5%) were obtained. The retention times were 14.265 minute and 18.705 minute respectively in chiral prep-HPLC chromatography.

Sources & evidence

ORD record
ord-42a06a1c20ae4c35ac20cbf0cd68ad7a
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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