3-Chloro-2-methylaniline → HCID 90229456, compound

HRID 1505776Notes

Reaction equation

HRID 1505776 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[O:8][C:7]([CH3:9])=[N:6][C:5]2=[C:10]([C:12]([OH:14])=O)[CH:11]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[Cl:46][C:47]1[C:48]([CH3:54])=[C:49]([CH:51]=[CH:52][CH:53]=1)[NH2:50]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[O:8][C:7]([CH3:9])=[N:6][C:5]2=[C:10]([C:12]([NH:50][C:49]2[CH:51]=[CH:52][CH:53]=[C:47]([Cl:46])[C:48]=2[CH3:54])=[O:14])[CH:11]=1

Participants

6

Reactant 4

HCID 68943-Chloro-2-methylanilineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 840315166-Bromo-2-methyl-1,3-benzoxazole-4-carboxylic acid

Product 1

HCID 90229456HCID 90229456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-2-methyl-1,3-benzoxazole-4-carboxylic acid (136 mg) in DMF (2 mL), were added HBTU (242 mg) and triethylamine (110 μL). To the mixture was added 3-chloro-2-methylaniline (76 μL) and it was stirred at room temperature over night. The reaction mixture was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain the titled compound (53 mg) as white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed sequentially with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified on silica gel column chromatography

Sources & evidence

ORD record
ord-3120c9da07fe40ffa1c9edc487de411b
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

Loading…