Diethyl chlorophosphate → HCID 178474149, compound

HRID 2225533Notes

Reaction equation

HRID 2225533 reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].NC1C=CC(C=CC(O)=O)=CC=1.P(Cl)(OCC)(OCC)=O.[CH3:37][N:38]([CH3:49])[CH2:39][CH2:40][NH:41][C@H:42]1[CH2:47][CH2:46][C@H:45]([CH3:48])[CH2:44][CH2:43]1>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(N(CC)CC)C>[CH3:37][N:38]([CH3:49])[CH2:39][CH2:40][N:41]([C@H:42]1[CH2:43][CH2:44][C@H:45]([CH3:48])[CH2:46][CH2:47]1)[C:11](=[O:13])[CH:10]=[CH:9][C:8]1[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 929283-(4-Aminophenyl)prop-2-enoic acidHCID 2515224-Acetylaminocinnamic acidHCID 178483797HCID 178483797, compound

Product 1

HCID 178474149HCID 178474149, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Using 2.0 g of 4-acetylaminocinnamic acid derived from 4-aminocinnamic acid by the acetylation thereof, 1.9 ml of diethyl chlorophosphate, 3.5 ml of triethylamine, 60 ml of methylene chloride, 2.3 ml of N-(2-dimethylaminoethyl)-trans-4-methylcyclohexylamine (Example 78), and 0.04 g of 4-dimethylaminopyridine, a reaction similar to that conducted in Example 81 was carried out. As a result, 2.08 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-4-acetylaminocinnamamide (a compound of the present invention) was obtained as white crystal, which had the following physiochemical properties:

Sources & evidence

ORD record
ord-55af0941fb234deaac8ad1dcd19fcab0
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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