m-Tolyl isocyanate → HCID 15670969, compound

HRID 1769721Notes

Reaction equation

[NH2:1][CH2:2][C:3]([N:5]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([C:21](=[O:27])[N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:28][C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1>>[CH2:23]([N:22]([CH2:25][CH3:26])[C:21]([CH:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3](=[O:4])[CH2:2][NH:1][C:36]([NH:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH3:28])[CH:30]=2)=[O:37])[CH2:16]1)=[O:27])[CH3:24]

Participants

Reactant 2

HCID 69303m-Tolyl isocyanate

HCID 20097170HCID 20097170, compound

Product 1

HCID 15670969HCID 15670969, compoundYield 37.7%

Procedure

Following a procedure analogous to that described in Example 106, but using 1.8 g of (RS)-2-amino-N-[2-(3-(N,N-diethylcarbamoyl)piperidino)-2-oxoethyl]-N-phenylacetamide and 0.64 g of 3-methylphenyl isocyanate as the starting material, 0.92 g of (RS)-N-[2-(3-(N,N-diethylcarbamoyl)piperidino)-2-oxoethyl]-2-[3-(3-methylphenyl)ureido]-N-phenyl acetamide melting at 156° C is obtained after recrystallization from an ethyl acetate/diisopropyl ether mixture (50/50 by volume).

Sources & evidence

ORD record: ord-0ad1476b7b0d47dbac70a8b80f45d1a8
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382590

Reaction notes

Loading…