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

HRID 1247139노트

반응식

HRID 1247139 반응식
[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]

참가 물질

10

반응물 5

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22dc2d3c1b024b038cd559f40769df37
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129245B2

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