Dichloromethane → N-{[(2S)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-N'-prop-2-ynylurea

HRID 1371447Notes

Reaction equation

HRID 1371447 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14](=[O:25])OC2C=CC([N+]([O-])=O)=CC=2)[CH2:7]1.[CH2:30]([NH2:33])[C:31]#[CH:32].ClCCl>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:5][N:6]1[CH2:11][CH2:10][O:9][C@@H:8]([CH2:12][NH:13][C:14]([NH:33][CH2:30][C:31]#[CH:32])=[O:25])[CH2:7]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 239041PropargylamineHCID 117750244-Nitrophenyl [(2S)-4-(3,4-dichlorobenzyl)morpholin-2-yl]methylcarbamate

Product 1

HCID 9968600N-{[(2S)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}-N'-prop-2-ynylureaYield 79.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Example 57 was prepared in an analogous manner to Example 43 from Intermediate 13 (0.1 g) and propargylamine (0.014 g) using dichloromethane and triethylamine at a temperature of 22° C. to yield the title compound (0.064 g).

Workup

  1. customat a temperature of 22° C.

Sources & evidence

ORD record
ord-bbcdf3fd5ef746529ddfeb67a1ec34e8
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

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