Ammonia → HCID 89544725, compound

HRID 2283391Notes

Reaction equation

HRID 2283391 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]([C:20]2[CH:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=2)=[O:19])[C:12]=1[F:27])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[NH3:29]>CO>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([C:18]([C:20]2[CH:21]=[N:22][C:23]([NH2:29])=[CH:24][CH:25]=2)=[O:19])[C:12]=1[F:27])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 89544738HCID 89544738, compound

Product 1

HCID 89544725HCID 89544725, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 2 {(R)-1-[4-Chloro-3-(6-chloro-pyridine-3-carbonyl)-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester (6.4 g, 15 mmol) was suspended in 7M NH3 in MeOH (32 mL) and split over 4 Reacti-vials and all heated at 100 degC overnight. The mixture was then evaporated down and purified by silica column, eluting 20-100% EtOAc in petroleum ether to give {(R)-1-[3-(6-amino-pyridine-3-carbonyl)-4-chloro-2-fluoro-phenyl]-propyl}-carbamic acid tert-butyl ester (3.1 g, 7.6 mmol, 51%). [MH]+ 408

Workup

  1. customsplit over 4 Reacti-vials
  2. temperatureall heated at 100 degC overnight
  3. customThe mixture was then evaporated down
  4. custompurified by silica column
  5. washeluting 20-100% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-aaad344b3f6b4333960c8a0d11b4ed91
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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