1H-Imidazole-1-propanamine → 6-(3,4-Difluorophenyl)-1-(3-imidazol-1-yl-propylcarbamoyl)-4-methyl-2-oxo-1,2,3,6-tetrahydro-pyrimidine-5-carboxylic Acid Methyl Ester

HRID 1066975Notes

Reaction equation

HRID 1066975 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14]([C:15](OC3C=CC([N+]([O-])=O)=CC=3)=[O:16])[C:13](=[O:27])[NH:12][C:11]([CH3:28])=[C:10]2[C:29]([O:31][CH3:32])=[O:30])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:33][CH2:34][CH2:35][CH2:36][N:37]1[CH:41]=[CH:40][N:39]=[CH:38]1>C(Cl)Cl>[CH3:32][O:31][C:29]([C:10]1[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[N:14]([C:15](=[O:16])[NH:33][CH2:34][CH2:35][CH2:36][N:37]2[CH:41]=[CH:40][N:39]=[CH:38]2)[C:13](=[O:27])[NH:12][C:11]=1[CH3:28])=[O:30]

Participants

4

Reactant 2

HCID 787361H-Imidazole-1-propanamineHCID 158957606-(3,4-Difluorophenyl)-4-methyl-5-methoxycarbonyl-1-(4-nitrophenoxy)carbonyl-2-oxo-1,2,3,6-tetrahydro-pyrimidine

Product 1

HCID 697276596-(3,4-Difluorophenyl)-1-(3-imidazol-1-yl-propylcarbamoyl)-4-methyl-2-oxo-1,2,3,6-tetrahydro-pyrimidine-5-carboxylic Acid Methyl EsterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(3,4-difluorophenyl)-4-methyl-5-methoxycarbonyl-1-(4-nitrophenoxy)carbonyl-2-oxo-1,2,3,6-tetrahydro-pyrimidine (100 mg, 0.22 mmol) and 1-(3-aminopropyl)imidazole (40 ml, 0.34 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 3 hours. The solvent was removed in vacuum. The residue was separated on preparative TLC (CHCl3/MeOH=100/15) to get the title compound (80 mg, 84% yield) as a white solid. Hydrochloride of title compound was made with HCl in ether. Calcd for C20H21N5O4F2+0.3 H2O: C, 54.74%; H, 4.99%; N, 15.89%. Found: C, 54.92%; H, 4.65%; N, 15.77%. M.P. of the salt: 221-224° C.

Workup

  1. customThe solvent was removed in vacuum
  2. customThe residue was separated on preparative TLC (CHCl3/MeOH=100/15)

Sources & evidence

ORD record
ord-1088b2e30acc4f01b6b7bcc6f6548001
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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