Hydrochloric Acid → 3-(3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)benzaldehyde

HRID 634417Notes

Reaction equation

HRID 634417 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:26]([C:28]3[O:29][C:30](=[O:53])[C:31]4[C:36]([C:37]=3[C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]5OC(C)(C)C(C)(C)[O:45]5)[CH:39]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH3:27])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:12]=3)[C:3]=12.Cl.C(Cl)Cl.O>CC#N>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:26]([C:28]3[O:29][C:30](=[O:53])[C:31]4[C:36]([C:37]=3[C:38]3[CH:39]=[C:40]([CH:41]=[CH:42][CH:43]=3)[CH:44]=[O:45])=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH3:27])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:12]=3)[C:3]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 1181311553-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-1H-isochromen-1-one2×

Product 1

HCID 1181314213-(3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)benzaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1-(4-amino-3-(3-(benzyloxy)-5-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl)-1H-isochromen-1-one (intermediate F5, 654 mg, 0,919 mmol) was dissolved in MeCN, then 2M HCl was added and the mixture was stirred overnight. DCM (25 ml) and water (25 ml) were added then phases were separated and the aqueous phase was washed again with 10 ml of DCM. The collected organic phases were concentrated to give the title compound (490 mg, 0.801 mmol, 87% yield) as a brown oil.

Workup

  1. customphases were separated
  2. washthe aqueous phase was washed again with 10 ml of DCM
  3. concentrationThe collected organic phases were concentrated

Sources & evidence

ORD record
ord-b5d1e79f66cd49b3b040a94e9df04f10
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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