1-Hydroxybenzotriazole → N-[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-3-methoxy-propionamide

HRID 655851

Reaction equation

HRID 655851 reaction equation
[NH2:1][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.[CH3:18][O:19][CH2:20][CH2:21][C:22](O)=[O:23].Cl.CN(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]([NH:1][C:22](=[O:23])[CH2:21][CH2:20][O:19][CH3:18])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1344423-Methoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 11996397N-[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-3-methoxy-propionamideYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (37 mg, 1.1 eq, 0.16 mmol) was added to a solution of 3-methoxypropionic acid (15.5 mg, 1.0 eq, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (25 mg, 1.0 eq, 0.16 mmol), 1-hydroxybenzotriazole (20 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 solvent was removed in vacuo. The resultant solid was washed with water and purified by semi-preparative HPLC to yield the title compound as a white solid (9.3 mg, 0.03 mmol, 20%). LCMS: [M+H]+=313, Rt=1.31 min, 100% purity.

Workup

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customsolvent was removed in vacuo
  3. washThe resultant solid was washed with water
  4. custompurified by semi-preparative HPLC

Sources & evidence

ORD record
ord-4ddad08c9e9b4e55a98e2ac84e8df074
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Linked notes

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