1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 75047711, compound

HRID 1951094Notes

Reaction equation

HRID 1951094 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].Cl.CN(C)CCCN=C=NCC.[Cl:27][C:28]1[CH:29]=[C:30]([CH:35]2[CH:39]([NH:40][CH3:41])[CH2:38][N:37]([C:42]([CH:44]3[CH2:49][CH2:48][N:47]([C:50]([C:52]4([CH3:55])[CH2:54][CH2:53]4)=[O:51])[CH2:46][CH2:45]3)=[O:43])[CH2:36]2)[CH:31]=[CH:32][C:33]=1[Cl:34]>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:40]([CH:39]2[CH:35]([C:30]3[CH:31]=[CH:32][C:33]([Cl:34])=[C:28]([Cl:27])[CH:29]=3)[CH2:36][N:37]([C:42]([CH:44]3[CH2:45][CH2:46][N:47]([C:50]([C:52]4([CH3:55])[CH2:54][CH2:53]4)=[O:51])[CH2:48][CH2:49]3)=[O:43])[CH2:38]2)[CH3:41])=[O:8])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 67025815[(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

Product 1

HCID 75047711HCID 75047711, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-chloro-3-(trifluoromethyl)benzoic acid (31 mg, 0.14 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27 mg, 0.14 mmol) was added at 0° C. under an atmosphere of nitrogen a solution {4-[(3SR,4RS)-3-(3,4-dichloro-phenyl)-4-methylamino-pyrrolidine-1-carbonyl]-piperidin-1-yl}-(1-methyl-cyclopropyl)-methanone (50 mg, 0.11 mmol) in dichloromethane (1 mL). The solution was stirred for 3 d in a thawing ice bath. The resulting solution was diluted with dichloromethane and was washed twice with water (10 mL). The aqueous layers were extracted with dichloromethane (10 mL) and the combined organic layers were dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:90:10) afforded the title compound (63 mg, 86%) as a light brown foam. MS m/e: 646.3 [M+H]+.

Workup

  1. washwas washed twice with water (10 mL)
  2. extractionThe aqueous layers were extracted with dichloromethane (10 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:90:10)

Sources & evidence

ORD record
ord-c631a3d40c0c45dc8b45759112edd44f
Source dataset
uspto-grants-2013_03
Patent number
US08404679B2

Reaction notes

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