Dimethylformamide → 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 586972노트

반응식

HRID 586972 반응식
CN(C=O)C.[CH2:6]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH2:28][CH2:27][C:26]([C:37](O)=[O:38])=[CH:25][C:24]=3[CH:40]=2)=[CH:16][CH:15]=1)[CH2:7][CH2:8][CH3:9].S(Cl)(Cl)=O.[CH3:45][N:46]([CH2:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1)[CH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1>ClCCl.O.C(N(CC)CC)C>[CH2:6]([O:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH2:28][CH2:27][C:26]([C:37]([NH:58][C:57]4[CH:56]=[CH:55][C:54]([CH2:53][N:46]([CH3:45])[CH:47]5[CH2:52][CH2:51][O:50][CH2:49][CH2:48]5)=[CH:60][CH:59]=4)=[O:38])=[CH:25][C:24]=3[CH:40]=2)=[CH:18][CH:19]=1)[CH2:7][CH2:8][CH3:9]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 9877845(4-Amino-benzyl)-methyl-(tetrahydro-pyran-4-yl)-amineHCID 69747253HCID 69747253, 화합물

생성물 1

HCID 223293307-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide수율 43.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

One droplet of DMF was added to a solution of 7-(4-butoxyethoxyphenyl)-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (50 mg) in dichloromethane (5 ml). Then, thionyl chloride (17 mg) was added at 0° C., the temperature was returned to room temperature, and the mixture was stirred under nitrogen atmosphere for 1 hour. Then, this solution was added to a solution of 4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]aniline (31 mg) and triethylamine (287 mg) in dichloromethane (15 ml) at 0° C. The mixture was stirred under nitrogen atmosphere at room temperature overnight, to the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:3) to give 7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-1-(2-pyridylmethyl)-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 73) (31 mg) as yellow amorphous.

후처리

  1. customwas returned to room temperature
  2. stirringThe mixture was stirred under nitrogen atmosphere at room temperature overnight, to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was separated
  8. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:3)

출처 및 근거

ORD 기록
ord-8240bea749504cfc8cc6ac6dcc8e6179
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936602B1

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