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

HRID 655842

反応式

HRID 655842 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e7b37e9c9bc4a31a77ed3c579b7a8ac
出典データセット
uspto-grants-2011_12
特許番号
US08071607B2

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