Hexane → HCID 118131067, compound

HRID 634467Notes

Reaction equation

HRID 634467 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:20]([C:22]3[O:23][C:24](=[O:42])[C:25]4[C:30]([C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:39]([CH3:41])[CH3:40])[CH:33]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:10]=[C:11]([C:12]3[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([F:19])[CH:13]=3)[C:4]=12.CCCCCC>C(O)C>[NH2:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]2[N:9]([CH:20]([C:22]3[O:23][C:24](=[O:42])[C:25]4[C:30]([C:31]=3[C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][N:39]([CH3:41])[CH3:40])[CH:33]=3)=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH3:21])[N:10]=[C:11]([C:12]3[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]([F:19])[CH:13]=3)[C:4]=12

Participants

4

Reactant 2

HCID 8058HexaneHCID 118131118HCID 118131118, compound

Product 1

HCID 118131067HCID 118131067, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemate 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(3-((dimethylamino)methyl)phenyl)-1H-isochromen-1-one hydrochloride (example 67, 0.558 g, 0.95 mmol) was dissolved in 10 ml of Ethanol and submitted to chiral resolution by Chiral preparative chromatography. Conditions: Column: Chiralpak AD-H (25×3 cm), 5 um; Mobile phase: n-Hexane/(Ethanol+0.1% isopropylamine) 75/25% v/v; Flow rate: 32 ml/min; DAD detection: 220 nm; Loop: 540 μl; Injection: 30 mg (each injection).

Sources & evidence

ORD record
ord-30bfba72326c410a8753f6303f445c9d
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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