Dichloromethane → 6-(3,4-Difluoro-phenyl)-1-[3-(3',6'-dihydro-[2,4']bip yridinyl-1'-yl)-propylcarbamoyl]-4-methyl-5-methoxycarbonyl-2-oxo-1,2,3,6-tetrahydropyrimidine hydrochloride

HRID 1066974Notes

Reaction equation

HRID 1066974 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].[N:33]1(CCCN)[CH2:38][CH:37]=[CH:36][CH:35]=[C:34]1[C:39]1[CH2:40][CH2:41][NH:42][CH2:43][CH:44]=1.C(Cl)[Cl:50]>>[ClH:50].[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[N:14]([C:15](=[O:16])[NH:12][CH2:11][CH2:10][CH2:9][N:42]3[CH2:43][CH:44]=[C:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=4)[CH2:40][CH2:41]3)[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]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 158957606-(3,4-Difluorophenyl)-4-methyl-5-methoxycarbonyl-1-(4-nitrophenoxy)carbonyl-2-oxo-1,2,3,6-tetrahydro-pyrimidineHCID 227251873-(3', 6'-dihydro-2'H-[2,4']bipyridyl-1-yl)propylamine

Product 1

HCID 698946336-(3,4-Difluoro-phenyl)-1-[3-(3',6'-dihydro-[2,4']bip yridinyl-1'-yl)-propylcarbamoyl]-4-methyl-5-methoxycarbonyl-2-oxo-1,2,3,6-tetrahydropyrimidine hydrochlorideYield 89%

Procedure

A solution of 6-(3,4-difluorophenyl)-4-methyl-5-methoxycarbonyl-1-(4-nitrophenoxy)carbonyl-2-oxo-1,2,3,6-tetrahydro-pyrimidine (20 mg, 0.045 mmol) and 3-(3′,6′-dihydro-2′H-[2,4′]bipyridyl-1-yl)propylamine (9.7 mg, 0.045 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 3 days. The solvent was removed in vacuum. The residue was separated on preparative TLC (CHCl3/MeOH=100/15) to get the title compound (21 mg, 89% yield) as a yellow solid. Hydrochloride salt was made with HCl in ether. M.P. of the salt: 242-244° C. Calcd for C27H29N5O4F2+2.0 HCl+1.05 CHCl3+1.05 ether: C, 48.32%; H, 5.35%; N, 8.74%. Found: C, 48.10%; H, 5.13%; N, 8.72%.

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-a70db0cdd321470ab1af8cb81bd993f0
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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