Butyric Acid → HCID 131729303, compound

HRID 655839Notes

Reaction equation

HRID 655839 reaction equation
N[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]3[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:18]([OH:23])(=O)[CH2:19][CH2:20][CH3:21].Cl.C[N:26](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.CO>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:4]3[CH:3]=[C:2]([CH:19]([CH2:20][CH3:21])[C:18]([NH2:26])=[O:23])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

7

Reactant 4

HCID 264Butyric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 131729303HCID 131729303, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (38 mg, 1.1 eq, 0.17 mmol) was added to a solution of butyric acid (13 mg, 1.0 eq, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 1.1 eq, 0.17 mmol), 1-hydroxybenzotriazole (21 mg, 1.0 eq, 0.15 mmol) in DMF (1 ml) which had been stirred for 10 minutes under an inert atmosphere. The reaction was stirred at room temperature for 18 hours, after which methanol (1 ml) was added and the solvents were removed in vacuo. The resultant solid purified by semi-preparative HPLC to yield the title compound as a white solid (5.4 mg, 0.018 mmol, 12%). LCMS: [M+H]+=297, Rt=1.48 min, 100% purity.

Workup

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customthe solvents were removed in vacuo
  3. customThe resultant solid purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-72fce7364d20477da77bb839a987df9d
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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