1,2-Dichloroethane → 4-(1-Cyclopropyl-1h-pyrazol-4-ylmethyl)-3'-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2h-[1,2']bipyrazinyl hydrochloride

HRID 220516ノート

反応式

HRID 220516 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[N:10][CH:11]=[CH:12][N:13]=2)=[CH:4][CH:3]=1.[CH:20]1([N:23]2[CH:27]=[C:26]([CH:28]=O)[CH:25]=[N:24]2)[CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:44]CCCl>>[ClH:44].[CH:20]1([N:23]2[CH:27]=[C:26]([CH2:28][N:17]3[CH2:16][CH2:15][N:14]([C:9]4[C:8]([C:5]5[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=5)=[N:13][CH:12]=[CH:11][N:10]=4)[CH2:19][CH2:18]3)[CH:25]=[N:24]2)[CH2:22][CH2:21]1

参加物

5

反応物 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 574169141-Cyclopropyl-1H-pyrazole-4-carboxaldehydeHCID 673669592-(4-Fluorophenyl)-3-(piperazin-1-yl)pyrazine

生成物 1

HCID 685946554-(1-Cyclopropyl-1h-pyrazol-4-ylmethyl)-3'-(4-fluoro-phenyl)-3,4,5,6-tetrahydro-2h-[1,2']bipyrazinyl hydrochloride収率 7%

実験手順

Dissolve 3′-(4-Fluoro-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.157 g, 0.608 mmol) in DCE (5 mL). Add 1-cyclopropyl-1H-pyrazole-4-carbaldehyde (0.354 g, 2.60 mmol) followed by sodium triacetoxyborohydride (0.193 g, 0.912 mmol) and stir at room temperature for 18 hr. Purify via SCX chromatography, followed by silica gel chromatography (eluting with 100:0 to 0:100 hexanes:ethyl acetate then 10:90 methanol:ethyl acetate), to give the free base of the title compound (16 mg, 7%). Dissolve this free base (0.014 g, 0.038 mmol) in methanol and add a solution of ammonium chloride (0.002 g, 0.038 mmol) in a minimal volume of methanol. Shake for 18 hr. at ambient temperature and concentrate to give the title compound (15 mg, 100%). MS (ES): m/z=379 [M+H]+.

後処理

  1. customPurify via SCX chromatography
  2. washeluting with 100:0 to 0:100 hexanes

出典と根拠

ORDレコード
ord-d9fb4863e5d84422b3c314b4781febe2
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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