4-Methylmorpholine → 2-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

HRID 1951582ノート

反応式

HRID 1951582 の反応式
CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[NH2:18][CH:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:20]([OH:22])[CH3:21].[Cl:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[C:32]([NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=1)=[O:33].Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C.O>[Cl:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[C:32]([NH:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([NH:18][CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]([OH:22])[CH3:21])=[O:40])=[CH:37][CH:36]=1)=[O:33]

参加物

9

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11329884-(2-Chlorobenzamido)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 123529221-Amino-1-phenylpropan-2-ol

生成物 1

HCID 574653742-chloro-N-(4-(((2-hydroxy-1-phenylpropyl)amino)carbonyl)phenyl)benzamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

to a room temperature mixture of 1-methylmorpholine (602 mg, 5.95 mmol), 1-hydroxybenzotriazole (322 mg, 2.38 mmol), 1-amino-1-phenylpropan-2-ol (300 mg, 1.98 mmol) and 4-(2-chlorobenzamido)benzoic acid (656 mg, 2.38 mmol) dissolved in 10 mL DMF was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (456 mg, 2.38 mmol) all in one portion. The reaction was left to stir at ambient temperature for 20 hours then poured into 30 mL water. The aqueous mixture was extracted with 50 mL 30% dichloromethane in diethyl ether. The organic extract was washed with 3×25 mL water then 20 mL brine, stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a white solid. The solid was suspended in hot ethyl acetate, cooled to room temperature and filtered, drying over a stream of air (658 mg, 81%). ESI+ m/z=409.1 [MH]+.

後処理

  1. waitThe reaction was left
  2. extractionThe aqueous mixture was extracted with 50 mL 30% dichloromethane in diethyl ether
  3. extractionThe organic extract
  4. washwas washed with 3×25 mL water
  5. stirring20 mL brine, stirred over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto afford a white solid
  9. temperaturecooled to room temperature
  10. filtrationfiltered
  11. customdrying over a stream of air (658 mg, 81%)

出典と根拠

ORDレコード
ord-597591de38454278973aa19458e72d93
出典データセット
uspto-grants-2013_03
特許番号
US08404722B2

反応ノート

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