Acetic Acid → HCID 118131118, compound

HRID 634466Notes

Reaction equation

HRID 634466 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:39])[C:24]4[C:29]([C:30]=3[C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[CH:34]=O)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:18])[CH:12]=3)[C:3]=12.CC(O)=O.[CH3:44][NH:45][CH3:46].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(Cl)[Cl:69]>C1COCC1>[ClH:69].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:19]([C:21]3[O:22][C:23](=[O:39])[C:24]4[C:29]([C:30]=3[C:31]3[CH:38]=[CH:37][CH:36]=[C:33]([CH2:34][N:45]([CH3:46])[CH3:44])[CH:32]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH3:20])[N:9]=[C:10]([C:11]3[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([F:18])[CH:12]=3)[C:3]=12

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 674DimethylamineHCID 6344DichloromethaneHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 118131062HCID 118131062, compound2×

Product 1

HCID 118131118HCID 118131118, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)benzaldehyde (Intermediate F2, 598 mg, 1.147 mmol), AcOH (131 μl, 2.293 mmol) and 2M dimethylamine (1.15 ml) solution in THF were dissolved in DCM (23 ml) followed by a spoon of anhydrous Na2SO4, and the mixture stirred rt for 15 min prior to add NaB(OAc)3H (1215 mg, 5.73 mmol). The resulting mixture was stirred at rt until complete conversion, then quenched with 1M HClaqueous (5 ml), filtered to remove insoluble materials, and the filtrate purified via reverse phase chromatography using a Biotage C18 60 g SNAP with a gradient of water and acetonitrile to give (prior to drying a small amount of 1M HCl aqueous was added) the title compound (460 mg, 68.3% yield) as white solid.

Workup

  1. stirringThe resulting mixture was stirred at rt until complete conversion
  2. customquenched with 1M HClaqueous (5 ml)
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. customthe filtrate purified via reverse phase chromatography
  6. customto give (prior
  7. dry with materialto drying a small amount of 1M HCl aqueous

Sources & evidence

ORD record
ord-bf405b2d86874ac4b6760b82786bf96a
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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