Acetic Acid → 3'-(4-Fluorophenyl)-4-[2-(1,3,5-triethyl-1H-pyrazol-4-yl)-ethyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride

HRID 220504노트

반응식

HRID 220504 반응식
[CH2:1]([N:3]1[C:7]([CH2:8][CH3:9])=[C:6]([CH2:10][CH:11]=O)[C:5]([CH2:13][CH3:14])=[N:4]1)[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:24][CH:25]=[CH:26][N:27]=2)=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(Cl)[Cl:53]>>[ClH:53].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([N:28]3[CH2:29][CH2:30][N:31]([CH2:11][CH2:10][C:6]4[C:5]([CH2:13][CH3:14])=[N:4][N:3]([CH2:1][CH3:2])[C:7]=4[CH2:8][CH3:9])[CH2:32][CH2:33]3)=[N:24][CH:25]=[CH:26][N:27]=2)=[CH:18][CH:17]=1

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazineHCID 86641649(1,3,5-Triethyl-1H-pyrazol-4-yl)-acetaldehyde

생성물 1

HCID 685947603'-(4-Fluorophenyl)-4-[2-(1,3,5-triethyl-1H-pyrazol-4-yl)-ethyl]-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine hydrochloride수율 83%

실험 절차

Combine (1,3,5-triethyl-1H-pyrazol-4-yl)-acetaldehyde (0.16 g, 0.82 mmol) and 3′-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.24 g, 0.91 mmol) in DCM (10 mL) and stir at room temperature for 15 min. Then add glacial acetic acid (0.07 mL, 1.23 mmol) and sodium triacetoxyborohydride (0.26 g, 1.23 mmol) and stir for 3 hr. at room temperature. Purify using SCX chromatography and further purify using silica gel chromatography (5% 7 M ammonia in methanol/DCM). Dissolve the free base in methanol (5 mL) and treat with ammonium chloride (0.037 g). Concentrate the resulting solution to give the title compound (0.032 g, 83%). MS: m/z=437.3[M+H]+.

후처리

  1. customat room temperature
  2. customPurify
  3. customfurther purify
  4. dissolutionDissolve the free base in methanol (5 mL)
  5. additiontreat with ammonium chloride (0.037 g)
  6. concentrationConcentrate the resulting solution

출처 및 근거

ORD 기록
ord-2e89aca8de5c43a093a6d2d04bea5ce2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202873B2

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