1-Hydroxybenzotriazole → HCID 57750252, compound

HRID 655840Notes

Reaction equation

HRID 655840 reaction equation
[NH2:1][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.[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:4]3[CH:3]=[C:2]([NH:1][C:22](=[O:23])[CH2:21][CH2:20][O:19][CH3:18])[CH:7]=[CH:6][CH:5]=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 119961041-(3-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Product 1

HCID 57750252HCID 57750252, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Title compound 11B, 1-(3-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 (5.8 mg, 0.02 mmol, 12%). LCMS: [M+H]+=313, Rt=1.35 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-a151421304e94b5baa9d7ef2028fd486
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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