Isopropylamine → HCID 11091484, compound

HRID 1870256Notes

Reaction equation

HRID 1870256 reaction equation
[C:1]([CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:18]=2[Cl:27])[CH2:8][CH2:7][CH2:6]1)(O)=[O:2].[CH:29]([NH2:32])([CH3:31])[CH3:30].P(C#N)(OCC)(OCC)=O.C(OCC)(=O)C>CN(C)C=O>[CH:29]([NH:32][C:1]([CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([C:16](=[O:28])[C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][CH3:26])=[CH:19][C:18]=2[Cl:27])[CH2:8][CH2:7][CH2:6]1)=[O:2])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 8857Ethyl AcetateHCID 76257Diethyl cyanophosphonateHCID 11784360HCID 11784360, compound

Product 1

HCID 11091484HCID 11091484, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the above product, 5-carboxymethyl-1-(4-n-propylamino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (800 mg) and isopropylamine (1.0 ml) in dimethylformamide (20 ml) is added dropwise diethyl cyanophosphate (391 mg) at room temperature. The mixture is stirred overnight, and thereto is added ethyl acetate. The mixture is washed with water, dried, concentrated, and purified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1), and further crystallized from diethyl ether to give 5-isopropylaminocarbonylmethyl-1-(4-n-propylamino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (840 mg).

Workup

  1. washThe mixture is washed with water
  2. customdried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (solvent; dichloromethane:methanol=50:1)
  5. customfurther crystallized from diethyl ether

Sources & evidence

ORD record
ord-1e54fe3e876f42ffbbc6a900acd63719
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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