Benzyl Bromide → HCID 58437115、化合物

HRID 1942326ノート

反応式

HRID 1942326 の反応式
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.C(OCC)(=O)C.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])=[N:6][CH:7]=1

参加物

7

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 218973345-Aminopyrazine-2-carboxylic acid

生成物 1

HCID 58437115HCID 58437115、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-aminopyrazine-2-carboxylic acid (493 mg, 3.54 mmol; Ark Pharm, Inc., Libertyville, Ill.) was stirred in dry N,N-dimethylformamide (3.0 mL) at room temperature under nitrogen. Solid potassium carbonate (742 mg, 5.37 mmol) was added, followed by benzyl bromide (0.43 mL, 3.6 mmol). The mixture was stirred for 22 hours and then diluted with ethyl acetate and water. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, filtered, and evaporated. The residue was purified by silica chromatography using a 40 g pre-packed column, eluting with ethyl acetate. The product fractions were combined, evaporated, and dried under high vacuum to afford (I-22a) (161.2 mg, 0.70 mmol, 20%): m/z 229.9 (M+H)+.

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica chromatography
  8. washeluting with ethyl acetate
  9. customevaporated
  10. customdried under high vacuum
  11. customto afford (I-22a) (161.2 mg, 0.70 mmol, 20%)

出典と根拠

ORDレコード
ord-25855e29913e478889c713240e398d32
出典データセット
uspto-grants-2013_03
特許番号
US08389552B2

反応ノート

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