4-Methylmorpholine → HCID 66795976, 화합물

HRID 2043764

반응식

HRID 2043764 반응식
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[N:17]3)[CH2:12][CH2:11]2)=[O:9])[N:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[CH:3]=1.CN1CCOCC1.[CH3:35][NH:36][C@H:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][CH2:38]1>ClCCl.O>[CH3:35][N:36]([C@H:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][CH2:38]1)[C:21]([C:18]1[CH:19]=[CH:20][N:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:8](=[O:9])[CH2:7][N:6]3[C:2]([CH3:1])=[CH:3][C:4]([C:24]([F:26])([F:25])[F:27])=[N:5]3)[CH2:15][CH2:14]2)[N:17]=1)=[O:23]

참가 물질

6

반응물 3

HCID 79724-MethylmorpholineHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amine2회HCID 674614591-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 66795976HCID 66795976, 화합물수율 14.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-1H-pyrazole-3-carboxylic acid (270 mg, 0.7 mmol) (i.e. the product of Example 18, Step E), N-(3-dimethylaminopropyl)-Y-ethylcarbodiimide hydrochloride (EDC) (147.61 mg, 0.77 mmol) and N-methylmorpholine (0.088 mL, 0.8 mmol) in 5 mL of dichloromethane was stirred at room temperature for 15 minutes. (1R)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (124.16 mg, 0.77 mmol) (i.e. the product of Example 6, Step A) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured in water, and the organic layer was subsequently washed with water, 1 M aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate, brine. The filtered reaction mixture was dried over magnesium sulfate and evaporated in vacuo. The crude product was purified by medium-pressure liquid chromatography on silica gel using 75-100 of ethyl acetate in hexanes as eluant to give 55 mg of the title compound, a compound of the present invention as an oil.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 16 h
  2. washthe organic layer was subsequently washed with water, 1 M aqueous hydrochloric acid, water, saturated aqueous solution of sodium bicarbonate, brine
  3. customThe filtered reaction mixture
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe crude product was purified by medium-pressure liquid chromatography on silica gel using 75-100 of ethyl acetate in hexanes as eluant

출처 및 근거

ORD 기록
ord-7fd2b15130bb49d28965f32349dc29ad
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586611B2

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