Thiophene-3-carboxylic acid → HCID 11996255, compound

HRID 655846Notes

Reaction equation

HRID 655846 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.[S:18]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19]1.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:23]([C:20]4[CH:21]=[CH:22][S:18][CH:19]=4)=[O:24])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

Participants

7

Reactant 4

HCID 6918Thiophene-3-carboxylic 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 11996255HCID 11996255, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (39 mg, 1.1 eq, 0.17 mmol) was added to a solution 3-thiophenecarboxylic acid (20 mg, 1.0 eq, 0.16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27 mg, 1.1 eq, 0.17 mmol), 1-hydroxybenzotriazole (21 mg, 1.0 eq, 0.16 mmol) in DMF (1 ml) which had been stirred for 10 minutes under an inert atmosphere. The reaction was stirred at room temperature for 17 hours, after which methanol (1 ml) was added, and the solvents were removed in vacuo. The resultant residue was absorbed onto silica and purified by column chromatography using DCM/MeOH (96:4) as eluent to yield the title compound as a white solid (10 mg, 0.03 mmol, 17%). LCMS: [M+H]+=337, Rt=1.58 min, 100% purity.

Workup

  1. stirringThe reaction was stirred at room temperature for 17 hours
  2. customthe solvents were removed in vacuo
  3. customThe resultant residue was absorbed onto silica
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-7df397a0ab424efaa638a8560cf74a6e
Source dataset
uspto-grants-2011_12
Patent number
US08071607B2

Reaction notes

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