Ammonium Chloride → HCID 68833154, compound

HRID 1454093Notes

Reaction equation

HRID 1454093 reaction equation
C([N:4](C(C)C)CC)(C)C.[CH2:10]([O:17][C:18](=[O:31])[CH:19]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[CH2:20][C:21](O)=[O:22])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[NH2:4][C:21](=[O:22])[CH2:20][CH:19]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[C:18]([O:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:31]

Participants

6

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 68831604HCID 68831604, compound

Product 1

HCID 68833154HCID 68833154, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Di-iso-propylethylamine (2.08 g, 2.80 mL, 16.0 mmol) was added in one portion to a stirred suspension of 4-(benzyloxy)-3-(4-bromophenyl)-4-oxobutanoic acid (1.45 g, 4.01 mmol), ammonium chloride (0.214 g, 4.01 mmol) and N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (1.68 g, 4.41 mmol) in dimethylformamide (20 mL) at room temperature under nitrogen. After stirring for 2 h the volatiles were evaporated and the residue partitioned between dichloromethane (50 mL) and aqueous hydrochloric acid solution (1.0 M; 50 mL). The phases were separated and the aqueous layer washed with dichloromethane (2×50 mL). The organic phases were combined, dried (magnesium sulfate) and evaporated to dryness. The residue was chromatographed on silica gel (10% methanol: dichloromethane) to give the title compound as a white solid (1.23 g, 85%). LC/MS: 3.14 min; z/e 362 and 364, calcd (M+1) 362 and 364. 1H NMR (400 MHz: DMSO-d6): 7.55 (2H), 7.30 (8H), 6.85 (1H), 5.05 (2H), 4.05 (1H), 2.90 (1H), 2.50 (1H).

Workup

  1. customwere evaporated
  2. customthe residue partitioned between dichloromethane (50 mL) and aqueous hydrochloric acid solution (1.0 M; 50 mL)
  3. customThe phases were separated
  4. washthe aqueous layer washed with dichloromethane (2×50 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel (10% methanol: dichloromethane)

Sources & evidence

ORD record
ord-996791058535489aa7e0b81e597548ea
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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