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

HRID 2204850

反応式

HRID 2204850 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8f62e9a84923410fbc193a93a6540439
出典データセット
uspto-grants-2016_06
特許番号
US09365557B2

関連ノート

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