Diisopropylethylamine → Netupitant

HRID 1017437노트

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HRID 1017437 반응식
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][C:6]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].C(N(C(C)C)C(C)C)C.[F:32][C:33]([F:51])([F:50])[C:34]1[CH:35]=[C:36]([C:44]([CH3:49])([CH3:48])[C:45](Cl)=[O:46])[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1.C(=O)(O)[O-].[Na+]>ClCCl>[F:32][C:33]([F:51])([F:50])[C:34]1[CH:35]=[C:36]([C:44]([CH3:49])([CH3:48])[C:45]([N:2]([CH3:1])[C:3]2[CH:4]=[N:5][C:6]([N:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)=[CH:7][C:8]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[O:46])[CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 158874123-Pyridinamine, N-methyl-4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-

생성물 1

HCID 6451149Netupitant수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
37.5 °C

실험 절차

A solution of 20 g (67.5 mmol) methyl-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]amine and 17.5 ml (101 mmol) N-ethyldiisopropylamine in 200 ml dichloromethane was cooled in an ice bath and a solution of 24 g (75 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 50 ml dichloromethane was added dropwise. The reaction mixture was warmed to 35-40° C. for 3 h, cooled to room temperature again and was stirred with 250 ml saturated sodium bicarbonate solution. The organic layer was separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to give 31.6 g (81%) of the title compound as white crystals. M.p. 155-157° C.

후처리

  1. temperaturecooled to room temperature again
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. customevaporated
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-239f61df2afa4900928c3518e41bd680
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479483B2

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