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

HRID 655851

반응식

HRID 655851 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4ddad08c9e9b4e55a98e2ac84e8df074
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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