Oxalyl chloride → 2-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)-5-iodobenzamide

HRID 1247139ノート

反応式

HRID 1247139 の反応式
[C:1]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[O-].[Na+].C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:28]=1[C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=1)=[O:30].C(N(CC)C(C)C)(C)C>CO.ClCCl.CN(C)C=O.CN(C1C=CN=CC=1)C>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:12]([NH:26][C:27]2[CH:42]=[CH:41][C:40]([I:43])=[CH:39][C:28]=2[C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][N:33]=2)=[O:30])=[O:14])[CH2:15][CH2:16]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

参加物

10

反応物 5

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 10942334Sodium MethoxideHCID 219063772-amino-N-(5-chloropyridin-2-yl)-5-iodobenzamide

生成物 1

HCID 219066352-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)-5-iodobenzamide収率 62%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirring solution of 1-Boc-isonipecotic acid (15.26 g, 66.55 mmol) in methanol (135 mL) was added sodium methoxide (3.8 g, 66.8 mmol). After stirring for 1 h, the solvent was removed in vacuo. A portion of the residue (8.92 g, 35.5 mmol) was suspended in dichloromethane (95 mL) and oxalyl chloride (4 mL, 45 mmol) was added, followed by a couple of drops of N,N-dimethylformamide. After stirring for 1 h, the solvent was removed in vacuo. The residue was suspended in dichloromethane (45 mL) and added to a solution of 2-amino-N-(5-chloropyridin-2-yl)-5-iodobenzamide (8.86 g, 23.7 mmol), N,N-diisopropylethylamine (5 mL, 28 mmol), and 4-(N,N-dimethylamino)pyridine (0.33 g, 2.7 mmol) in dichloromethane (50 mL). After stirring 19 h, the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was slurried in diethyl ether and filtered to give 8.6 g (62%) of a pink solid.

後処理

  1. customthe solvent was removed in vacuo
  2. stirringAfter stirring for 1 h
  3. customthe solvent was removed in vacuo
  4. stirringAfter stirring 19 h
  5. customthe reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-22dc2d3c1b024b038cd559f40769df37
出典データセット
uspto-grants-2006_10
特許番号
US07129245B2

反応ノート

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