2-Dimethylaminopyridine → HCID 9865190, compound

HRID 1267934Notes

Reaction equation

HRID 1267934 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[C:15]([CH3:23])=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][NH2:28].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CN(C1C=CC=CN=1)C.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([NH:13][C:14]2[C:15]([CH3:23])=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH:28][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[O:19])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 5

HCID 218852-DimethylaminopyridineHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 18542421HCID 18542421, compound

Product 1

HCID 9865190HCID 9865190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[2-(3,4-difluorophenylamino)acetylamino]-2-methylbenzoic acid (0.2 g), N,N-dimethylethylenediamine (0.08 ml), bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP®) (0.34 g), dimethylaminopyridine (0.07 g) and N,N-diisopropylethylamine (0.31 ml) in dimethylformamide (5 ml) was stirred at room temperature under N2 for 18 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic phase was washed with water and brine, dried (MgSO4) and evaporated. The crude product was triturated with diethyl ether. The resultant solid was triturated with ethyl acetate and filtered. Yield 70 mg.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was triturated with diethyl ether
  6. customThe resultant solid was triturated with ethyl acetate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-478e01b551bc4070ab84ee3a6110e5f5
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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