Triethylamine → 3-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide

HRID 2204850

반응식

HRID 2204850 반응식
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([NH:20][NH2:21])=[O:19].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:9]([NH:21][NH:20][C:18]([C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH3:12])=[O:19])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27600843-Methylthiophene-2-carbohydrazideHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

생성물 1

HCID 594723013-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide수율 36.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (13.26 g, 60.82 mmol) and 3-methylthiophene-2-carbohydrazide (10 g, 60.82 mmol) in DMF (95.00 mL) cooled in an ice bath was added Et3N (7.385 g, 10.17 mL, 72.98 mmol) followed by TBTU (23.43 g, 72.98 mmol) portionwise after complete addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and water (50 mL). The layers were separated and the organic extracts washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4 and concentrated to leave a brown solid (7.85 g, 36% yield) which was used directly in the next step without further purification.

후처리

  1. temperaturecooled in an ice bath
  2. additionportionwise after complete addition
  3. customThe layers were separated
  4. washthe organic extracts washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f62e9a84923410fbc193a93a6540439
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365557B2

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