4-Methylmorpholine → HCID 66795976、化合物

HRID 2043764

反応式

HRID 2043764 の反応式
[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]

参加物

6

反応物 3

HCID 79724-MethylmorpholineHCID 7128544(R)-N-Methyl-1,2,3,4-tetrahydronaphthalen-1-amine2 回HCID 674614591-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 66795976HCID 66795976、化合物収率 14.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7fd2b15130bb49d28965f32349dc29ad
出典データセット
uspto-grants-2013_11
特許番号
US08586611B2

関連ノート

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