Methylamine → HCID 67374974, compound

HRID 1517530Notes

Reaction equation

HRID 1517530 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([O:15][CH3:16])=[CH:7][C:3]=1[C:4](O)=[O:5].CN.C1C=CC2N(O)N=[N:25][C:23]=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.Cl>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([O:15][CH3:16])=[CH:7][C:3]=1[C:4]([NH:25][CH3:23])=[O:5]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67374784HCID 67374784, compound

Product 1

HCID 67374974HCID 67374974, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

step 1—To a solution of 58 (150 mg) in DMF (10 mL) cooled to 0° C. was added MeNH2 (0.52 mL, 2.0 M in THF,), HOBt (140 mg) and EDCI (200 mg). The reaction mixture was then stirred overnight at RT then diluted with 1N aq HCl solution and extracted with EtOAc. The organic layer was washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (0 to 10% MeOH) to afford 140 mg of 2-bromo-4-tert-butyl-5-methoxy-N-methyl-benzamide (60) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed sequentially with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with a MeOH/DCM gradient (0 to 10% MeOH)

Sources & evidence

ORD record
ord-1b9afb6961dd4b72b1cdc489cbe30cbc
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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