Oxalyl chloride → N-(1-Benzyl-3-iodo-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79257ノート

反応式

HRID 79257 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]([OH:17])=O)=[CH:13][N:14]=[C:8]2[CH:7]=1.C(Cl)(=O)C(Cl)=O.[CH2:24]([N:31]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]([NH2:40])[C:34]=2[C:33]([I:41])=[N:32]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O.C(OCC)C>[CH2:24]([N:31]1[C:39]2[C:34](=[C:35]([NH:40][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][C:8]4=[N:14][CH:13]=3)=[O:17])[CH:36]=[CH:37][CH:38]=2)[C:33]([I:41])=[N:32]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

8

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 667820257-(2-Methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 672595921-benzyl-3-iodo-1H-indazol-4-amine2 回

生成物 1

HCID 53261960N-(1-Benzyl-3-iodo-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

7-(2-M ethoxyethoxy)imidazo[1,2-a]pyridine-3-carboxylic acid (150 mg; 0.635 mmol) was suspended in methylene chloride (2 mL), with stirring, under an atmosphere of dry nitrogen. Oxalyl chloride (0.698 mmol) was added as a 2N solution in dichloromethane (0.35 mL). A catalytic amount of dimethylformamide (1 drop) was added. The mixture was stirred until effervescence had ceased (30 minutes). 1-Benzyl-3-iodo-1H-indazol-4-amine (product of step G) (222 mg; 0.635 mmol) was added as a solution in dichloromethane (2 mL). Diisopropylethylamine (213 mg; 0.29 mL; 1.65 mmol) was added and the mixture was stirred under nitrogen in a sealed vessel for 24 hours. A thick suspension formed. The mixture was diluted with diethyl ether (20 mL) and the solids were collected by filtration. The solids were washed with ether and water and then dried under vacuum. This gave the desired product, N-(1-Benzyl-3-iodo-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide, as an off white solid (139 mg). MS (APCI), positive scan, m/z=568.1 (M+H).

後処理

  1. stirringThe mixture was stirred until effervescence
  2. custom(30 minutes)
  3. stirringthe mixture was stirred under nitrogen in a sealed vessel for 24 hours
  4. customA thick suspension formed
  5. filtrationthe solids were collected by filtration
  6. washThe solids were washed with ether and water
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-7527926577ea4777bbc79a3dfe8d5093
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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