Diisopropylethylamine → HCID 89691099, compound

HRID 2202896Notes

Reaction equation

HRID 2202896 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH:9][CH3:10])=[CH:4][CH:3]=1.[CH3:11]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:44][C:45]1([F:51])[CH2:47][CH:46]1C(O)=O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:10]([CH:46]3[CH2:47][C:45]3([F:51])[F:44])[N:8]([CH3:11])[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27828232,2-Difluorocyclopropane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112985934-Bromo-N1-methylbenzene-1,2-diamine

Product 1

HCID 89691099HCID 89691099, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromo-N′-methylbenzene-1,2-diamine (300 mg), HATU (567 mg), N,N-diisopropylethylamine (0.255 ml), 2,2-difluorocyclopropanecarboxylic acid (182 mg) and DMF (10 ml) was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, passed through NH silica gel pad and concentrated in vacuo. The precipitate was washed with IPE/hexane, collected by filtration and dried in vacuo to give the title compound (255 mg) as a yellow solid.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe precipitate was washed with IPE/hexane
  8. filtrationcollected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-bcfc387528214212b7e85185ee80c703
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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