Triethylamine → 3'-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 220555ノート

反応式

HRID 220555 の反応式
Cl.Cl.[Cl:3][C:4]1[C:5]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1.[CH2:16]([N:18]1[CH:22]=[C:21]([CH:23]=O)[C:20]([CH3:25])=[N:19]1)[CH3:17].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(=O)(O)[O-].[Na+].C(O)(=O)C>[Cl:3][C:4]1[C:5]([N:10]2[CH2:11][CH2:12][N:13]([CH2:23][C:21]3[C:20]([CH3:25])=[N:19][N:18]([CH2:16][CH3:17])[CH:22]=3)[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][N:9]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 5732031-ethyl-3-methyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866416583'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl dihydrochloride

生成物 1

HCID 866416653'-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl収率 65%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 63651,1-Dichloroethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Combine 3′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl dihydrochloride (2.21 g, 8.18 mmol), 1-ethyl-3-methyl-1H-pyrazole-4-carbaldehyde (1.3 g, 9.40 mmol) and triethylamine (1.31 mL, 9.40 mmol) in dichloroethane (50 mL). Add glacial acetic acid (0.85 mL) followed by sodium triacetoxyborohydride (2.99 g, 14.1 mmol). Stir at room temperature for 20 hr. Dilute with saturated aq. sodium bicarbonate then extract three times using DCM. Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM), to give 3′-chloro-4-(1-ethyl-3-methyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl as a yellow oil (1.702 g, 65%). MS (ES): m/z=321 [M+H]+.

後処理

  1. extractionthen extract three times
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 4.5:95.5 methanol (with 2 M ammonia):DCM)

出典と根拠

ORDレコード
ord-442138f678e14c09b20cd62562e58b2f
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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