3,4-Dichlorophenethylamine → HCID 59729936、化合物

HRID 131000

反応式

HRID 131000 の反応式
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:24][CH2:25][NH2:26].[BH4-].[Na+]>CO>[Cl:20][C:21]1[CH:22]=[C:23]([CH2:24][CH2:25][NH:26][CH2:18][C:16]2[CH:15]=[CH:14][C:3]([O:4][C:5]3[N:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=3)=[C:2]([F:1])[CH:17]=2)[CH:27]=[CH:28][C:29]=1[Cl:30]

参加物

5

反応物 3

HCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydrideHCID 597300135-(2-Fluoro-4-formylphenoxy)pyrazine-2-carboxamide

生成物 1

HCID 59729936HCID 59729936、化合物収率 44%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Place 5-(2-fluoro-4-formylphenoxy)pyrazine-2-carboxamide (Example 737, Part E) (0.400 g, 1.53 mmol), 3,4-dichlorophenethylamine (0.320 g, 1.68 mmol) and 3 {acute over (Å)} molecular sieves in a vial. Add methanol (7.7 mL), cap and stir overnight. Add NaBH4 (0.058 g, 1.53 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 0% to 15% (2.0 M NH3 in methanol) in 80% (ethyl acetate in hexanes). Concentrate the fractions containing the product. Take the solid up in dichloromethane (100 mL) and wash with 1.0 N NaOH (2×25 mL) to give the title compound (0.293 g, 44%): TOF MS ES+ 435.1 (M+H)+, HRMS calcd for C20H18N4O2FCl2 435.0791 (M+H)+, found 435.0815, time 0.53 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min, 20-95% over 18], tR=12.8 min, 100% purity.

後処理

  1. customDry the column in a vacuum oven at room temperature
  2. customPurify
  3. washby eluting through a 40 g ISCO® column with 0% to 15% (2.0 M NH3 in methanol) in 80% (ethyl acetate in hexanes)
  4. concentrationConcentrate the fractions
  5. additioncontaining the product
  6. washwash with 1.0 N NaOH (2×25 mL)

出典と根拠

ORDレコード
ord-84ecfbc2c52e4fdf9b05a03f9f3eac7e
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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