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

HRID 655851

反応式

HRID 655851 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ddad08c9e9b4e55a98e2ac84e8df074
出典データセット
uspto-grants-2011_12
特許番号
US08071607B2

関連ノート

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