Butyric Acid → [4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramide

HRID 655850

Reaction equation

HRID 655850 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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:5]3[CH:6]=[CH:7][C:2]([CH:19]([CH2:20][CH3:21])[C:18]([NH2:26])=[O:23])=[CH:3][CH:4]=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 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 131729304[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramideYield 19.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Title compound 11A, 1-(4-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 (8.5 mg, 0.029 mmol, 19%). LCMS: [M+H]+=297, Rt=1.45 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-dafc2ac356984b20b9b2bb4c5534eee8
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Linked notes

Loading…