Pyridine → HCID 66894164, 화합물

HRID 252754노트

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HRID 252754 반응식
CS[C:3]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[CH:4][C:5]#[N:6].[NH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[CH2:32][N:33](CC)CC>CN(C1C=CN=CC=1)C>[NH2:25][C:30]1[CH:29]=[CH:28][CH:27]=[CH:26][C:32]=1[NH:33][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][NH:14][C:3]([NH:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:5]#[N:6])=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8471Triethylamine2회HCID 655264-(Aminomethyl)Benzoic AcidHCID 66893771HCID 66893771, 화합물

생성물 1

HCID 66894164HCID 66894164, 화합물수율 44%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
55 °C

실험 절차

To a mixture of 3-methylsulfanyl-3-(pyridin-4-ylamino)-acrylonitrile (0.2 g, 1.0 mmol), 4-aminomethyl-benzoic acid (0.173 g, 1.14 mmol), DMAP (1 mg) and Et3N (0.14 ml, 1.0 mmol) was added dry pyridine (0.5 ml). The resulting stirring mixture was heated to 55° C. for 4.5 hrs., additional Et3N (0.14 ml) was added and mixture was heated from 75° C. to 90° C. over a period of −30 hrs. When the reaction was complete, pyridine was partially removed in vacuo and the crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc) to afford the desired product as an off-white solid (130 mg, 44%).

후처리

  1. temperaturemixture was heated from 75° C. to 90° C. over a period of −30 hrs
  2. custompyridine was partially removed in vacuo
  3. customthe crude was purified by column chromatography (gradient of EtOAc to 20% MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-c46ae51ce4c34c0ca830c0e3f00b8208
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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