Formaldehyde → N-[(1RS,2SR)-2-(Cyclobutyl-methyl-amino)-cyclohexyl]-2-methoxy-4,6-bis-trifluoromethyl-benzamide

HRID 659243ノート

反応式

HRID 659243 の反応式
[CH:1]1([NH:5][C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]2[NH:12][C:13](=[O:30])[C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([C:24]([F:27])([F:26])[F:25])=[CH:16][C:15]=2[O:28][CH3:29])[CH2:4][CH2:3][CH2:2]1.C=O.[C:33](=O)([O-])[O-].[Na+].[Na+]>C(O)=O>[CH:1]1([N:5]([CH3:33])[CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]2[NH:12][C:13](=[O:30])[C:14]2[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:17]([C:24]([F:25])([F:26])[F:27])=[CH:16][C:15]=2[O:28][CH3:29])[CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 58062857cis-N-(2-Cyclobutylamino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide

生成物 1

HCID 76683026N-[(1RS,2SR)-2-(Cyclobutyl-methyl-amino)-cyclohexyl]-2-methoxy-4,6-bis-trifluoromethyl-benzamide収率 38%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
110 °C

実験手順

cis-N-(2-Cyclobutylamino-cyclohexyl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide (example 16, 118 mg, 0.27 mmol) was dissolved in 2 mL formic acid. Formaldehyde (36% in water, 0.06 mL, 0.81 mmol) was added and the reaction mixture was stirred at 110° C. over night. The reaction mixture was basified by slow addition of 10 ml 1N sodium carbonate solution. The mixture was extracted three times with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→110:10:1) yielded the title compound as a white solid (46 mg, 38%), MS: m/e=453.2 [(M+H)+].

後処理

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. customThe combined organic phases were dried on sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→110:10:1)

出典と根拠

ORDレコード
ord-d72662dd91784b31b702c01df00b802f
出典データセット
uspto-grants-2011_12
特許番号
US08080541B2

反応ノート

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