Dichloromethane → HCID 117839333, compound

HRID 1477721Notes

Reaction equation

HRID 1477721 reaction equation
ClCCl.[Cl:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]2[CH:15]=[N:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[N:12][C:11]2=[O:29])=[CH:7][C:6]=1[O:32]C.B(Br)(Br)Br>O>[Cl:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]2[CH:15]=[N:14][C:13]([N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH2:20][CH2:21]3)=[N:12][C:11]2=[O:29])=[CH:7][C:6]=1[OH:32]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 117839942HCID 117839942, compound

Product 1

HCID 117839333HCID 117839333, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dichloromethane solution (1.0 mL) of 1-(4-chloro-3-methoxybenzyl)-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (10.0 mg, 0.0232 mmol) synthesized in Synthesis Example 141, 1M boron tribromide (1.00 mL, 1.00 mmol) was added at −78° C. and while elevating gradually the temperature of the resultant mixture to room temperature, the mixture was stirred for 3 hours. After the completion of the reaction, to the reaction solution, water was added and extraction with ethyl acetate from the reaction solution was performed. The organic layer was dried and was concentrated under reduced pressure and the resultant solid was washed with ethyl acetate to obtain the title compound (6.00 mg, yield: 62%).

Workup

  1. additionwas added at −78° C.
  2. customto room temperature
  3. customAfter the completion of the reaction
  4. extractionextraction with ethyl acetate from the reaction solution
  5. customThe organic layer was dried
  6. concentrationwas concentrated under reduced pressure
  7. washthe resultant solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-c0beb3b80257415fbbe0521f2c1e9dba
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…