1,2-Dichloroethane → 1-{4-[4-(5-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride

HRID 220517노트

반응식

HRID 220517 반응식
[N:1]1([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=3)=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:22][C:23]1[N:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:26]=[CH:25][C:24]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:50]CCCl>>[ClH:50].[CH3:22][C:23]1[N:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:26]=[CH:25][C:24]=1[CH2:34][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=3)=[N:11][CH:10]=[CH:9][N:8]=2)[CH2:2][CH2:3]1

참가 물질

5

반응물 4

HCID 111,2-DichloroethaneHCID 27764375-Methyl-1-phenyl-1H-pyrazole-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685951741-[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-ethanone

생성물 1

HCID 685952071-{4-[4-(5-Methyl-1-phenyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl]-phenyl}-ethanone hydrochloride수율 78%

실험 절차

Dissolve 1-[4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-ethanone (0.250 g, 0.885 mmol) in 1,2 dichloroethane (4 mL). Add 5-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (1.5 eq., 0.250 g, 1.33 mmol). Stir for 30 min. Add sodium triacetoxyborohydride (2.0 eq., 0.375 g, 1.77 mmol). Stir at room temperature for 48 hr. Purify by SCX column followed by normal phase chromatography with a gradient of 100% EtOAc to 5% 7N ammonia in methanol/EtOAc to give the freebase of the title compound, (0.312 g, 78% yield). MS (ES): m/z=453.2[M+H]. Dissolve in a mixture of acetonitrile (2 mL) and water (3 mL). Add aq. 1N HCl (1 eq., 0.69 mmol, 0.69 mL). Freeze the solution to −78° C. in a dry-ice/acetone bath. Place the solution in the lyophilizer for 48 hr. to give the title compound (0.268 g, 80% yield). MS (ES): m/z=453.2 [M+H]+.

후처리

  1. stirringStir at room temperature for 48 hr
  2. customPurify by SCX column

출처 및 근거

ORD 기록
ord-ca87527e461048acb70ed2058a6972ee
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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