1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-(3,4-Difluorophenyl)-1,6-dihydro-5-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propylaminocarbonyl)-1-methoxymethyl-2,4-dimethylpyrimidine

HRID 1066976Notes

Reaction equation

HRID 1066976 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=2)[N:8]([CH2:18][O:19][CH3:20])[C:7]([CH3:21])=[N:6][C:5]=1[CH3:22])([OH:3])=O.Cl.CN(C)CCCN=C=NCC.[CH3:35][O:36][C:37]([C:39]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:43][N:42]([CH2:45][CH2:46][CH2:47][NH2:48])[CH2:41][CH2:40]1)=[O:38]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:17][C:12]1[CH:11]=[C:10]([CH:9]2[N:8]([CH2:18][O:19][CH3:20])[C:7]([CH3:21])=[N:6][C:5]([CH3:22])=[C:4]2[C:1]([NH:48][CH2:47][CH2:46][CH2:45][N:42]2[CH2:41][CH2:40][C:39]([C:37]([O:36][CH3:35])=[O:38])([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:44][CH2:43]2)=[O:3])[CH:15]=[CH:14][C:13]=1[F:16]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 106838831-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidineHCID 227251935-Carboxy-6-(3,4-difluoro-phenyl)-1,6-dihydro-1-methoxymethyl-2,4-dimethylpyrimidine

Product 1

HCID 227252176-(3,4-Difluorophenyl)-1,6-dihydro-5-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propylaminocarbonyl)-1-methoxymethyl-2,4-dimethylpyrimidineYield 32%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-carboxy-6-(3,4-difluoro-phenyl)-1,6-dihydro-1-methoxymethyl-2,4-dimethylpyrimidine (0.13 g, 0.42 mmol.), 4-dimethylaminopyridine (0.1 g, 0.84 mmol.), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.16 g, 0.82 mmol.) and CH2Cl2 (5 mL) was stirred at room temperature for 0.5 hr. After the addition of 3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)propylamine (0.17 g, 0.62 mmol.), the mixture was refluxed overnight. To the mixture was added another 25 mL of CH2Cl2 and washed with saturated NH4Cl solution. After removal of the solvent, the residue was flash chramotographed over silica gel (eluent: 80:20 v/v ethyl acetate-methanol) to give the title compound in 32% yield (0.075 g) as a pale yellow solid: mp 53-57° C. Anal. Calcd. for C31H38F2N4O4.0.25CHCl3: C, 62.71; H, 6.44; N, 9.36. Found: C, 62.62; H, 6.79; N, 9.19.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washwashed with saturated NH4Cl solution
  3. customAfter removal of the solvent

Sources & evidence

ORD record
ord-ce2aa563261341f6b6a0cc9298cc6cf9
Source dataset
uspto-grants-2001_06
Patent number
US06245773B1

Reaction notes

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