5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 353804

反応式

HRID 353804 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][C:20](OCC)=[O:21].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[NH2:9][C:8]1[C:3]2[CH:4]=[N:5][N:6]([CH3:7])[C:2]=2[NH:1][C:20](=[O:21])[C:19]=1[C:11]1[NH:10][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=1

参加物

5

反応物 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 1354961414-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Amino-1-methyl-1H-pyrazole-4-carbonitrile (1.0 eq) and ethyl 1H-benzimidazol-2-ylacetate (1.0 eq) were dissolved in THF and dried over sieves. LiHMDS (3 eq) was added dropwise and the mixture stirred for 18 hours. The mixture was filtered and diluted with EtOAc, then washed with an aqueous saturated NH4Cl solution. The aqueous layer was washed with EtOAc (3×), and the organic layers combined, dried over MgSO4, and concentrated yielding pure product. LC/MS m/z 281.0 (MH+), Rt 1.41 minutes.

後処理

  1. customdried over sieves
  2. filtrationThe mixture was filtered
  3. additiondiluted with EtOAc
  4. washwashed with an aqueous saturated NH4Cl solution
  5. washThe aqueous layer was washed with EtOAc (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customyielding pure product

出典と根拠

ORDレコード
ord-1c679456dc4d4e8aaad9c958ecf5ab34
出典データセット
uspto-grants-2004_06
特許番号
US06756383B2

関連ノート

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