Triethylamine → Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

HRID 1362933

反応式

HRID 1362933 の反応式
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28](O)=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28]([NH:10][NH:9][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:8])=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1

参加物

7

反応物 5

HCID 8471TriethylamineHCID 11112Nicotinic acid, hydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

生成物 1

HCID 59830438Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of nicotinic acid hydrazide (35 mg, 0.25 mmol) in DMF (5 mL) was added triethylamine (88 μL, 0.64 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 8, 50 mg, 0.25 mmol), HOBt (34 mg, 0.25 mmol) and EDCI (50 mg, 0.28 mmol). The mixture was allowed to stir at rt for 16 h. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give an oil, which was purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1) to give the title compound. m/z (ES+)=316 [M+H]+; RT=2.62 min.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil, which
  6. customwas purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1)

出典と根拠

ORDレコード
ord-289e93d2f1644254a1d4659a32b7a4aa
出典データセット
uspto-grants-2011_02
特許番号
US07884112B2

関連ノート

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