Hydrochloric Acid → HCID 22280169, compound

HRID 1063706Notes

Reaction equation

HRID 1063706 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[CH:8][C:7]=1[CH3:26].[H-].[Na+].[F:30][C:31]([F:41])([F:40])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1.Cl>CN(C=O)C>[CH3:13][O:12][C:10]1[C:9]([S:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:36][C:35]3[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:40])[F:41])=[CH:39][CH:38]=3)[CH:18]=2)=[CH:8][C:7]([CH3:26])=[C:6]([CH:11]=1)[O:5][CH2:4][C:3]([OH:2])=[O:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 20827018HCID 20827018, compound

Product 1

HCID 22280169HCID 22280169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound 54A (0.300 g, 0.778 mmol) was dissolved in 5 ml DMF. NaH was added and stirred for ½ h. 4-trifluoromethylbenzyl bromide (0.223 g, 0.934 mmol) was added and the reaction was stirred for 1.5 h. 10 ml 2N HCl was added to pH<4. The DMF solution was partitioned between 30 ml water and 30 ml ethyl acetate. The organic solution was washed 2×30 ml water 1×30 ml brine, dried over sodium sulfate, decanted, concentrated and purified by MPLC to give the title product. MS m/z 544 (M+1).

Workup

  1. stirringthe reaction was stirred for 1.5 h
  2. customThe DMF solution was partitioned between 30 ml water and 30 ml ethyl acetate
  3. washThe organic solution was washed 2×30 ml water 1×30 ml brine
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. custompurified by MPLC

Sources & evidence

ORD record
ord-b75d75d31626480e9aeb8887025e3a43
Source dataset
uspto-grants-2005_11
Patent number
US06964983B2

Reaction notes

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