Hydrochloric Acid → HCID 118131184, compound

HRID 634520Notes

Reaction equation

HRID 634520 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:25]([C:27]3[O:28][C:29](=[O:43])[C:30]4[C:35]([C:36]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH3:26])[N:9]=[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[C:15]([O:17][Si](C(C)(C)C)(C)C)[CH:16]=3)[C:3]=12.[ClH:44]>CCO>[ClH:44].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:25]([C:27]3[O:28][C:29](=[O:43])[C:30]4[C:35]([C:36]=3[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH3:26])[N:9]=[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[C:15]([OH:17])[CH:16]=3)[C:3]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123359983HCID 123359983, compound

Product 1

HCID 118131184HCID 118131184, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(1-(4-amino-3-(5-((tert-butyldimethylsilyl)oxy)pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one single enantiomer (intermediate S.2, first eluted enantiomer under the conditions described above, 0.070 g, 0.118 mmol) was dissolved in a solution of 1M HCl in EtOH (0.38 mL) and the mixture was stirred at RT for 5 h. The volatiles were removed under reduced pressure and the residue was purified by flash chromatography on silica gel cartridge (DCM to DCM:MeOH=95:5) to afford title compound as a white solid (0.059 g, 0.115 mmol, 97%). This compound proved to be the second eluted enantiomer under Chiral HPLC conditions of Method A9: Rt=15.4 min, ee>99%.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel cartridge (DCM to DCM:MeOH=95:5)

Sources & evidence

ORD record
ord-e19ed23748144a62ab96e381727ce8d2
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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