Triethylamine → HCID 19607984, compound

HRID 745113Notes

Reaction equation

HRID 745113 reaction equation
[C:1]([CH2:4][O:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])=[CH:20][CH:19]=2)[CH2:9][CH2:8][CH2:7]1)(O)=[O:2].[NH:35]1[CH2:40][CH2:39][S:38][CH2:37][CH2:36]1.P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O.O>[S:38]1[CH2:39][CH2:40][N:35]([C:1]([CH2:4][O:5][CH:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([C:17](=[O:34])[C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[CH3:32])=[CH:20][CH:19]=3)[CH2:9][CH2:8][CH2:7]2)=[O:2])[CH2:36][CH2:37]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67164ThiomorpholineHCID 76257Diethyl cyanophosphonateHCID 19607815HCID 19607815, compound

Product 1

HCID 19607984HCID 19607984, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-carboxymethoxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.50 g) in dimethylformamide (60 ml) are added successively thiomorpholine (0.66 ml), diethyl cyanophosphate (0.89 g) and triethylamine (1.37 ml) with stirring under ice-cooling. The mixture is stirred for 30 minutes under ice-cooling, and at room temperature for 20 minutes. Water (60 ml) is added to the reaction solution, and extracted with dichloromethane. The extract is dried over magnesium sulfate, and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:2→3:1), and recrystallized from ethyl acetate/n-hexane to give 5-(thiomorpholinocarbonylmethoxy)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.60 g) as white powder, m.p. 235°-237° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred for 30 minutes under ice-
  3. temperaturecooling
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract is dried over magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=5:2→3:1)
  8. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-36f187dd6a834c238369c375f5bd03b1
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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