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

HRID 706664
ノート
印刷プレビュー

反応式

HRID 706664 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:16]([C:19]([O-:21])=O)=[CH:17][N:18]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1.[Li+].C(Cl)(=O)C(Cl)=O.[CH2:29]([N:36]1[C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([NH2:45])[C:39]=2[CH:38]=[N:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH2:29]([N:36]1[C:44]2[C:39](=[C:40]([NH:45][C:19]([C:16]3[N:13]4[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[CH:11][C:12]4=[N:18][CH:17]=3)=[O:21])[CH:41]=[CH:42][CH:43]=2)[CH:38]=[N:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 213273171-benzyl-1H-indazol-4-amineHCID 67261208Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

生成物 1

HCID 57384337N-(1-benzyl-1H-indazol-4-yl)-7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxamide収率 12.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒

実験手順

To a suspension of lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate (42 mg, 0.142 mmol) in DCM were added oxalyl chloride (1.1 equivalents) and a drop of DMF. The mixture was stirred until gas evolution stopped. To the reaction mixture were then added 1-benzyl-1H-indazol-4-amine (31.6 mg, 0.142 mmol) and Hunig's base (1.2 equivalents). The reaction was stirred at ambient temperature for two hours and then concentrated. The residue was triturated with diethyl ether followed by chromatographic purification on silica with 10% MeOH/DCM as eluent to provide 8.6 mg of the desired product as a white solid. MS (ES+APCI) m/z=497 (M+H) detected.

後処理

  1. stirringThe reaction was stirred at ambient temperature for two hours
  2. concentrationconcentrated
  3. customThe residue was triturated with diethyl ether
  4. customfollowed by chromatographic purification on silica with 10% MeOH/DCM as eluent

出典と根拠

ORDレコード
ord-235f6587fddf42a99d70b111099b9c60
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174981B2

反応ノート

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