Dimethylformamide → HCID 22313088, compound

HRID 966145Notes

Reaction equation

HRID 966145 reaction equation
CCN=C=NCCCN(C)C.[CH:12]1[CH:13]=[CH:14][C:15]2N(O)N=[N:18][C:16]=2C=1.Cl.[O:23]([NH2:25])[CH3:24].[C:26](O)([C:28]([F:31])(F)F)=O.CN(C)[CH:35]=[O:36]>C(OCC)(=O)C.ClCCl.C(N(CC)CC)C>[NH2:18][C:16]1[C:28]([F:31])=[CH:26][C:13]([CH3:12])=[C:14]([CH:15]=1)[C:35]([NH:25][O:23][CH3:24])=[O:36]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 22313088HCID 22313088, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound B (820 mg, 3 mmol) in dimethyl formamide (10 mL) were added EDCI (700 mg, 3.6 mmol), HOBt (460 mg, 3 mmol), methoxylamine hydrochloride (370 mg, 3.6 mmol) and triethylamine (0.9 mL). After stirring for 1 h at RT, the mixture was diluted with ethyl acetate and washed with water, dried and concentrated. The solid obtained was dissolved in dichloromethane (2.5 mL) and TFA (2.5 mL) was added. After 2 h, the mixture was concentrated, the residue was dissolved in ethyl acetate and washed with saturated NaHCO3 to afford 5-amino-2-methyl-4-fluoro-N-methoxybenzamide (520 mg). LC/MS; (M+H)+=199.2.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe solid obtained
  5. waitAfter 2 h
  6. concentrationthe mixture was concentrated
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with saturated NaHCO3

Sources & evidence

ORD record
ord-63a22c8e15664c43acab603855a0b7c1
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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