1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 87158406, compound

HRID 2206905Notes

Reaction equation

HRID 2206905 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N:10]2[CH2:14][CH2:13][C:12]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[CH:11]2[OH:33])=[N:7][C:8]=1[Br:9].[F:34][C:35]([F:41])([F:40])[CH2:36][C:37](O)=[O:38].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[F:28][C:25]([F:26])([F:27])[C:23]1[CH:24]=[C:19]([C:12]2([C:15]([F:17])([F:18])[F:16])[CH2:13][CH2:14][N:10]([C:6]3[N:7]=[C:8]([Br:9])[C:3]([CH2:2][NH:1][C:37](=[O:38])[CH2:36][C:35]([F:41])([F:40])[F:34])=[CH:4][CH:5]=3)[CH:11]2[OH:33])[CH:20]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:22]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 87158396HCID 87158396, compound

Product 1

HCID 87158406HCID 87158406, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The mixture of 1-[5-(aminomethyl)-6-bromopyridin-2-yl]-3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-2-ol (90 mg), 3,3,3-trifluoropropionic acid (31 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (62 mg), dichloromethane (10 ml) and a catalytic amount of 4-dimethylaminopyridine was stirred overnight at room temperature. Upon the completion of the reaction, the solvent was distilled off and the residue was purified by silica gel chromatography to obtain N-[(6-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-2-bromopyridin-3-yl)methyl]-3,3,3-trifluoropropanamide (70 mg).

Workup

  1. customUpon the completion of the reaction
  2. distillationthe solvent was distilled off
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8dde0f729966453a9df056ea755507ed
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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