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 1387388Notes

Reaction equation

HRID 1387388 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-4b85f77ce269400c8dbaa89acd1281dc
Source dataset
uspto-grants-2001_07
Patent number
US06268369B1

Reaction notes

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