Sodium Hydroxide → HCID 68683848, compound

HRID 2234375Notes

Reaction equation

HRID 2234375 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[C:3]=1F.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[F:30][P-](F)(F)(F)(F)F.[NH2:37][CH:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([C:6]([NH:37][CH:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]2)=[O:7])=[C:9]([F:30])[CH:10]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27375314-Amino-1-methylpiperidineHCID 193583604-Bromo-2,3-difluorobenzoic acid

Product 1

HCID 68683848HCID 68683848, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromo-difluorobenzoic acid (Fluorochem; 3.0 g, 12.66 mol) and HBTU (5.3 g, 13.92 mol) were added to DMF (80 mL), to this was added the required 4-amino-1-methylpiperidine (Fluorochem; 1.59 g, 13.93 mol) and DIPEA (5.0 mL, 27.85 mol), the reaction was stirred for 48 hours, after which the solvent was removed in vacuo to yield a brown gum. The gum was treated with 2.0 M NaOH (50 mL) and extracted with DCM (3×200 ml). Combined extracts were dried and solvent removed in vacuo to yield a dark orange gum which was recrystallised from hot acetonitrile to give the title compound as a white solid (1.9 g, 45%)

Workup

  1. customafter which the solvent was removed in vacuo
  2. customto yield a brown gum
  3. extractionextracted with DCM (3×200 ml)
  4. customCombined extracts were dried
  5. customsolvent removed in vacuo
  6. customto yield a dark orange gum which
  7. customwas recrystallised from hot acetonitrile

Sources & evidence

ORD record
ord-fc8805cdd2e94dd7af3c2bd5e26a4ccd
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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