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 220504ノート

反応式

HRID 220504 の反応式
[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

参加物

6

反応物 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

生成物 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 hydrochloride収率 83%

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2e89aca8de5c43a093a6d2d04bea5ce2
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

反応ノート

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