1-Hydroxybenzotriazole → 1-Methyl-1H-imidazole-2-carboxylicacid[3-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amide

HRID 655842

반응식

HRID 655842 반응식
[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][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[C:24](O)=[O:25].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:24]([C:20]4[N:19]([CH3:18])[CH:23]=[CH:22][N:21]=4)=[O:25])[CH:7]=[CH:6][CH:5]=3)[N:9]=[CH:10][C:11]=12

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11996104HCID 11996104, 화합물

생성물 1

HCID 577502601-Methyl-1H-imidazole-2-carboxylicacid[3-(4-amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-amide수율 8.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

Title compound 11B, 1-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (30 mg, 1.1 eq, 0.13 mmol) was added to a solution 1-methyl-1H-imidazole-2-carboxylic acid (15 mg, 1.0 eq, 0.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (20 mg, 1.1 eq, 0.13 mmol), 1-hydroxybenzotriazole (16 mg, 1.0 eq, 0.12 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 residue was then triturated with methanol and the resultant solid was isolated by filtration to yield the title compound as a yellow solid (3 mg, 0.01 mmol, 8%). LCMS: [M+H]+=335, Rt=1.48 min, 94% purity.

후처리

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customthe solvents were removed in vacuo
  3. customThe residue was then triturated with methanol
  4. customthe resultant solid was isolated by filtration

출처 및 근거

ORD 기록
ord-0e7b37e9c9bc4a31a77ed3c579b7a8ac
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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