Triethylamine → HCID 15409145, 화합물

HRID 849479노트

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HRID 849479 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 15409145HCID 15409145, 화합물수율 66.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid (0.170 g) and 1-(4-methoxyphenyl)piperazine (Aldrich; 0.165 g) in dichloromethane (4mL) 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. 1HNMR (CDCl3) δ 3.16, 3.78, 3.97, 4.47, 6.86, 6.94, 7.21, 7.56, 8.10, 8.20.

후처리

  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

출처 및 근거

ORD 기록
ord-97f051843fc849898839cd96538dcb88
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06013654

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