Triethylamine → HCID 15409145、化合物

HRID 1416238ノート

反応式

HRID 1416238 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([N:25]3[CH2:24][CH2:23][N:22]([C:19]4[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=4)[CH2:27][CH2:26]3)=[O:13])[N:10]=2)[CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2697221-(4-Methoxyphenyl)piperazineHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acid

生成物 1

HCID 15409145HCID 15409145、化合物収率 66.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid (0.170 g) and 1-(4-methoxyphenyl)piperazine (Aldrich; 0.165 g) in dichloromethane (4 mL) are added diethyl cyanophosphonate (Aldrich; 0.157 mL) and triethylamine (0.144 mL), followed by DMF (2 mL). After stirring overnight, the mixture is quenched with aqueous sodium bicarbonate and then partitioned between dichloromethane and aqueous sodium bicarbonate. The organic layers are filtered through sodium sulfate and concentrated, and the residue is chromatographed on silica gel using methanol/dichloromethane (2/98) to give 0.212 g of 1-[(6-chloroimidazo[1,2-a]pyridin-2-yl)carbonyl]-4-(4-methoxyphenyl)piperazine; mp 180-181° C.: IR (mineral oil) 1620, 1517, 1237, 1246, 1230 cm-1. 1H NMR (CDCl3) δ3.16, 3.78, 3.97, 4.47, 6.86, 6.94, 7.21, 7.56, 8.10,8.20.

後処理

  1. customthe mixture is quenched with aqueous sodium bicarbonate
  2. custompartitioned between dichloromethane and aqueous sodium bicarbonate
  3. filtrationThe organic layers are filtered through sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel

出典と根拠

ORDレコード
ord-62e7d426063445229323c54c70bb7967
出典データセット
uspto-grants-1999_06
特許番号
US05912246

反応ノート

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