Potassium Carbonate → HCID 22714353, compound

HRID 1636914Notes

Reaction equation

HRID 1636914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)([C:19]4[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=4)[OH:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>O.C1COCC1>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:25]2[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=2)([OH:18])[C:19]2[N:23]([CH3:24])[CH:22]=[N:21][CH:20]=2)=[CH:13][C:12]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:9]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22714354HCID 22714354, compound

Product 1

HCID 22714353HCID 22714353, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

TiCl3 /15% in H2O (200 ml) was added at room temperature to a solution of intermediate (6-c) (38 g) in THF (300 ml). The mixture was stirred at room temperature for 90 minutes. The mixture was poured out on ice, basified with K2CO3, filtered over celite, washed with ethyl acetate and decanted. The organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1 and 95/5/0.1), yielding 18.7 g (49%) of (±)-[2-amino-5-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]phenyl](3-chlorophenyl)methanone (interm. 6-d).

Workup

  1. additionThe mixture was poured out on ice
  2. filtrationfiltered over celite
  3. washwashed with ethyl acetate
  4. customdecanted
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1 and 95/5/0.1)

Sources & evidence

ORD record
ord-f56abfd462ae46ffa536ad79569202fa
Source dataset
uspto-grants-2000_03
Patent number
US06037350

Reaction notes

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