Dimethylformamide → HCID 15614939, compound

HRID 620348Notes

Reaction equation

HRID 620348 reaction equation
C[N:2](C)C=O.C(Cl)(=O)C(Cl)=O.[F:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:27][CH3:28])[C:19]=2[C:23]([F:26])([F:25])[F:24])[C:14]=1[C:29]([N:31]([C:36]([O:38][CH3:39])=[O:37])[CH2:32][C:33]([OH:35])=O)=[O:30]>C(Cl)Cl>[F:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:27][CH3:28])[C:19]=2[C:23]([F:25])([F:24])[F:26])[C:14]=1[C:29]([N:31]([CH2:32][C:33]([NH2:2])=[O:35])[C:36]([O:38][CH3:39])=[O:37])=[O:30]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 129764N-((2-Fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl)carbonyl)-N-(methoxycarbonyl)glycine

Product 1

HCID 15614939HCID 15614939, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl formamide (6 μL, 0.067 eq) and oxalyl chloride (130 μL, 1.2 eq) were added to a stirred solution of N-[[2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-(methoxycarbonyl)glycine in anhydrous methylene chloride (2.5 mL) at 0° C. under a dry nitrogen atmosphere. After 5 minutes, the reaction was warmed to room temperature. After 13/4 hours, the organics were removed. The residue was dissolved in anhydrous ether (30 mL) at 0° C. and ammonia gas was bubbled in for 1 minute. The reaction was immediately quenched with hexane (30 mL). The solid was collected by suction filtration and suspended in ethyl acetate (75 mL). The ethyl acetate phase was washed with water (2×25 mL), dried with magnesium sulfate, and the ethyl acetate was removed. The solid was combined with that from another run and recrystallized in chloroform:petroleum ether to provide the title compound as a white solid (325 mg, 54% combined yield), m.p. 199°-202° C.

Workup

  1. customAfter 13/4 hours, the organics were removed
  2. dissolutionThe residue was dissolved in anhydrous ether (30 mL) at 0° C.
  3. customammonia gas was bubbled in for 1 minute
  4. customThe reaction was immediately quenched with hexane (30 mL)
  5. filtrationThe solid was collected by suction filtration
  6. washThe ethyl acetate phase was washed with water (2×25 mL)
  7. dry with materialdried with magnesium sulfate
  8. customthe ethyl acetate was removed
  9. customrecrystallized in chloroform

Sources & evidence

ORD record
ord-57729ee4b4344fbc9750eb0d117942af
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

Loading…