Ammonium Chloride → HCID 89544451, compound

HRID 2283420Notes

Reaction equation

HRID 2283420 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]([CH3:18])([CH3:17])[CH2:13][C:14]([OH:16])=O)[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21].CC[N:30](C(C)C)C(C)C.[Cl-].[NH4+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11][C:12]([CH3:17])([CH3:18])[CH2:13][C:14]([NH2:30])=[O:16])[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89544672HCID 89544672, compound

Product 1

HCID 89544451HCID 89544451, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step 2 To a stirred solution of 3-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}-propyl]amino}-3-methylbutanoic acid (0.023 g, 0.0585 mmol), iPr2NEt (0.0714 mL, 0.41 mmol) and ammonium chloride (0.0157 g, 0.293 mmol) in DMF (0.351 mL) at 0° C. was added HATU (0.0334 g, 0.0878 mmol). The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was poured into EtOAc and washed with water (×3). The organic extract was dried (Na2SO4), filtered and concentrated. The material was converted to the HCl salt and triturated with EtOAc providing 3-{[(1R)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propyl]amino}-3-methylbutanamide, 0.013 g, 52%.

Workup

  1. washwashed with water (×3)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customtriturated with EtOAc

Sources & evidence

ORD record
ord-aaf25da884694a8f941a2ac75be64567
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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