Ammonium Chloride → HCID 118071315, compound

HRID 920825Notes

Reaction equation

HRID 920825 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([C:14]([F:17])([F:16])[F:15])[CH2:12][N:11]2[N:18]=[C:19]([I:24])[C:20]([C:21](O)=[O:22])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].C[N:28](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:21]([C:20]1[C:19]([I:24])=[N:18][N:11]2[CH2:12][CH:13]([C:14]([F:17])([F:16])[F:15])[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][C:10]=12)(=[O:22])[NH2:28]

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 118062800HCID 118062800, compound

Product 1

HCID 118071315HCID 118071315, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 346E (0.12 g, 0.260 mmol) in DMF (1 mL) was added NH4Cl (0.028 g, 0.520 mmol), HATU (0.099 g, 0.260 mmol) and DIPEA (0.136 mL, 0.781 mmol) under nitrogen and the resulting solution was stirred at RT for 16 h. The reaction mixture was poured into water and the aqueous layer was extracted with EtOAc (2×25 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 3% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 346F as a white solid (0.07 g, 50%). MS(ES): m/z=460.9 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 3% MeOH in CHCl3)
  5. additionFractions containing the product
  6. customevaporated

Sources & evidence

ORD record
ord-ce68b3879c64414ab574407589f7ced3
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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