Triethylamine → HCID 178490554, compound

HRID 2225604Notes

Reaction equation

HRID 2225604 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:25])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([OH:22])=O)=[C:14]([O:23][CH3:24])[CH:13]=2)[CH2:4][CH2:3]1.P(Cl)(OCC)(OCC)=O.C(N(CC)CC)C.[N:42]1([CH:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([N:51]3[CH2:52][CH2:53][CH:48]([N:42]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)[CH2:49][CH2:50]3)=[O:22])=[C:14]([O:23][CH3:24])[CH:13]=2)=[O:25])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 786071,4'-BipiperidineHCID 178490558HCID 178490558, compound

Product 1

HCID 178490554HCID 178490554, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Using 1.9 g of N-(trans-4-methylcyclohexyl)-4-(carboxymethoxy)-3-methoxycinnamamide (Example 172), 1.2 ml of diethyl chlorophosphate, 2.3 ml of triethylamine, 0.92 g of 4-piperidinopiperidine, 0.04 g of 4-dimethylaminopyridine, and 100 ml of methylene chloride, a reaction similar to that conducted in Example 188 was carried out. As a result, 1.51 g of 1-{4-{2-[N-(trans-4-methylcyclohexyl)carbamoyl]vinyl}-2-methoxyphenoxyacetyl}-4-piperidinopiperidine (a compound of the present invention) was obtained as white crystal, which had the following physiochemical properties:

Workup

  1. customa reaction similar to

Sources & evidence

ORD record
ord-c6857929628f497d894802c02b8edbdc
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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