Ethanol → HCID 89545057, compound

HRID 2283443Notes

Reaction equation

HRID 2283443 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[C:6]([F:16])[C:5]([C@H:17]([NH:20][CH2:21][C:22]2[N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=[N:25][CH:26]=2)[CH2:18][CH3:19])=[CH:4][CH:3]=1.Cl.CCOC(C)=O.C(O)C>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:17]([NH:20][CH2:21][C:22]2[NH:23][CH:24]=[N:25][CH:26]=2)[CH2:18][CH3:19])=[C:6]([F:16])[C:7]=1[C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 89545415HCID 89545415, compound

Product 1

HCID 89545057HCID 89545057, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To (6-Chloro-2-fluoro-3-{(R)-1-[(3-trityl-3H-imidazol-4-ylmethyl)-amino]-propyl}-phenyl)-pyridin-3-yl-methanone (0.208 g, 0.33 mmol) suspended in acetone (2 ml) treated with saturated HCl/EtOAc, ethanol added till all in solution stirred at ambient for 18 hours, concentrated then purified by Prep HPLC to give [(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl](1H-imidazol-5-ylmethyl)amine (0.07 g), MS: [M+H] 373

Workup

  1. additionadded till all in solution
  2. concentrationconcentrated
  3. customthen purified by Prep HPLC

Sources & evidence

ORD record
ord-27f7e90cdd0141ff89689d49de48da2b
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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