1,2-Dichloroethane → (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

HRID 2085439Notes

Reaction equation

HRID 2085439 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:14]([C:15]([OH:17])=O)=[C:13]([CH2:18][O:19][CH3:20])[NH:12][C:11](=[O:21])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)CCl.CN1CCOCC1.[N+:33]([C:36]1[CH:37]=[C:38]([C:42]2[CH2:43][CH2:44][N:45]([CH2:48][CH2:49][CH2:50][NH2:51])[CH2:46][CH:47]=2)[CH:39]=[CH:40][CH:41]=1)([O-:35])=[O:34]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:14]([C:15]([NH:51][CH2:50][CH2:49][CH2:48][N:45]3[CH2:44][CH:43]=[C:42]([C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([N+:33]([O-:35])=[O:34])[CH:37]=4)[CH2:47][CH2:46]3)=[O:17])=[C:13]([CH2:18][O:19][CH3:20])[NH:12][C:11](=[O:21])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 10780384(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylic acidHCID 220487383-(4-(3-Nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)-1-propanamine

Product 1

HCID 69875018(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylic acid (1.2 eq), EDC (1.5 Eq.), N-methylmorpholine (2.0 Eq.) in dichloromethane was stirred at room temperature for 15 minutes, followed by addition of 3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)-1-propanamine (1.0 eq.) to the reaction mixture. The resulting solution was stirred for 18 hours, concentrated and chromatographed on silica to give (4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-N-[3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propyl]-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxamide.

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica

Sources & evidence

ORD record
ord-da776e08f24643c1ada699043eb7bc14
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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