Benzyl Bromide → HCID 58437115, 화합물

HRID 1011498노트

반응식

HRID 1011498 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 58437115HCID 58437115, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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%)

출처 및 근거

ORD 기록
ord-c0edaf7c98514f019f043bfa2d9f8846
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977367B2

반응 노트

불러오는 중…