Triethylamine → N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamide

HRID 1269776

反応式

HRID 1269776 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([NH:26][CH3:27])[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]([CH3:27])[C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:12])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

8

反応物 6

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 42484541H-Indazole-5-carboxylic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 22933863N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamide収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the 1H-indazole-5-carboxylic acid (281 mg, 1.73 mmol) obtained in Reference Example 1 in N,N-dimethylformamide (10 ml) were added 1-benzyl-N-methylpiperidin-4-amine (390 mg, 1.91 mmol), triethylamine (0.29 ml, 2.08 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide monohydrochloride (499 mg, 2.60 mmol) and hydroxybenzotriazole (281 mg, 2.08 mmol), and the resulting mixture was stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction solution, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate→chloroform/methanol) to obtain N-(1-benzylpiperidin-4-yl)-N-methyl-1H-indazole-5-carboxamide (502 mg, 83%).

後処理

  1. extractionfollowed by extraction with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate→chloroform/methanol)

出典と根拠

ORDレコード
ord-f98bff7e9af44eb890aeb8d2f479d887
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

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