Butyric Acid → [4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramide

HRID 655850

반응식

HRID 655850 반응식
N[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.[C:18]([OH:23])(=O)[CH2:19][CH2:20][CH3:21].Cl.C[N:26](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]([CH:19]([CH2:20][CH3:21])[C:18]([NH2:26])=[O:23])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

참가 물질

7

반응물 4

HCID 264Butyric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

생성물 1

HCID 131729304[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramide수율 19.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (38 mg, 1.1 eq, 0.17 mmol) was added to a solution of butyric acid (13 mg, 1.0 eq, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 1.1 eq, 0.17 mmol), 1-hydroxybenzotriazole (21 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 the solvents were removed in vacuo. The resultant solid purified by semi-preparative HPLC to yield the title compound as a white solid (8.5 mg, 0.029 mmol, 19%). LCMS: [M+H]+=297, Rt=1.45 min, 100% purity.

후처리

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customthe solvents were removed in vacuo
  3. customThe resultant solid purified by semi-preparative HPLC

출처 및 근거

ORD 기록
ord-dafc2ac356984b20b9b2bb4c5534eee8
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071607B2

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