Triethylamine → HCID 178490121, compound

HRID 2225549Notes

Reaction equation

HRID 2225549 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH:17]=[CH:18][C:19]([OH:21])=O)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(OCC)(OCC)=O.C(N(CC)CC)C.[CH3:40][N:41]([CH3:52])[CH2:42][CH2:43][NH:44][C@H:45]1[CH2:50][CH2:49][C@H:48]([CH3:51])[CH2:47][CH2:46]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:40][N:41]([CH3:52])[CH2:42][CH2:43][N:44]([C@H:45]1[CH2:46][CH2:47][C@H:48]([CH3:51])[CH2:49][CH2:50]1)[C:19]([CH:18]=[CH:17][CH:16]=[CH:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:10]([O:22][CH3:23])[CH:11]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 542250435-[4-(Benzyloxy)-3-methoxyphenyl]penta-2,4-dienoic acidHCID 178483797HCID 178483797, compound

Product 1

HCID 178490121HCID 178490121, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Using 4g of 4-(4-benzyloxy-3-methoxyphenyl)-1,3-butadiene-1-carboxylic acid disclosed in the literature [R. Backstrom, E. Honkanen, A. Pippuri, P. Kairisalo, J. Pystynen, K. Heinola, E. Nissinen, I. Linden, P. T. Mannisto, S. Kaakkola, and P. Pohto, J. Med. Chem., 32, 841-848 (1989)], 3 ml of diethyl chlorophosphate, 3.5 ml of triethylamine, 150 ml of methylene chloride, 4 ml of N-(2-dimethylaminoethyl)-trans-4-methylcyclohexylamine (Example 78), and 0.5 g of 4-dimethylaminopyridine, a reaction similar to that conducted in Example 81 was carried out. As a result, 3.81 g of N-(2-dimethylaminoethyl)-N-(trans-4-methylcyclohexyl)-4-(4-benzyloxy-3-methoxyphenyl)-1,3-butadiene-1-carboxamide (a compound of the present invention) was obtained as a pale yellow oil, which had following physiochemical properties:

Sources & evidence

ORD record
ord-8dd2d4ef639c4a159ba18d057ec27a92
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

Loading…