3-Chloro-2-methylaniline → HCID 90229388, compound

HRID 1505804Notes

Reaction equation

HRID 1505804 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[NH:7][C:6]2[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[C:11]([C:12]([OH:14])=O)[C:5]=2[N:4]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[Cl:52][C:53]1[C:54]([CH3:60])=[C:55]([CH:57]=[CH:58][CH:59]=1)[NH2:56]>CN(C=O)C.C(OCC)(=O)C.C1COCC1>[Cl:52][C:53]1[C:54]([CH3:60])=[C:55]([NH:56][C:12]([C:11]2[C:5]3[N:4]=[C:3]([N:2]([CH3:1])[CH3:18])[NH:7][C:6]=3[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[O:14])[CH:57]=[CH:58][CH:59]=1

Participants

7

Reactant 4

HCID 68943-Chloro-2-methylanilineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90229440HCID 90229440, compound

Product 1

HCID 90229388HCID 90229388, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of 2-(dimethylamino)-6-nitro-1H-benzimidazole-4-carboxylic acid (520 mg) and HBTU (1.03 g) in DMF (6 mL), were added N,N-diisopropylethylamine (942 μL) and 3-chloro-2-methylaniline (323 μl), and the mixture was stirred at room temperature for 15 hours. The reaction mixture was diluted with ethyl acetate-THF (1:1), washed with brine, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with MeOH to obtain the titled compound (650 mg) as a yellow solid.

Workup

  1. washwashed with brine
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with MeOH

Sources & evidence

ORD record
ord-aaed48bacf8f405bb2715f0c76392623
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

Loading…