Dichloromethane → 5-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

HRID 1788047Notes

Reaction equation

HRID 1788047 reaction equation
[B-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)([C:22]4[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=4)[OH:21])[CH:18]=3)[N:13]3[N:35]=[N:36][N:37]=[C:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1.C(Cl)Cl>CO>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)([C:22]4[N:26]([CH3:27])[CH:25]=[N:24][CH:23]=4)[OH:21])[CH:18]=3)[N:13]3[N:35]=[N:36][N:37]=[C:12]3[NH:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22959485VertellusHCID 688635845-(3-chlorophenyl)-alpha-(4-fluorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

Product 1

HCID 1363420815-(3-chlorophenyl)-alpha-(4-fluorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanolYield 21.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroborate (0.001 mol) was added portionwise at room temperature to a mixture of intermediate 8 (0.001 mol) in methanol (5 ml). The mixture was stirred at room temperature for 2 hours and poured out into ice water. DCM was added. The organic layer was washed with water, separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried in a vacuo. The residue (0.35 g, 70%) was crystallized from ethanol. The precipitate was filtered off and dried in a vacuo, yielding 0.105 g (21%) of 5-(3-chlorophenyl)-α-(4-fluorophenyl)-4,5-dihydro-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 9), mp. 230° C.

Workup

  1. washThe organic layer was washed with water
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from 2-propanone
  7. filtrationThe precipitate was filtered off
  8. customdried in a vacuo
  9. customThe residue (0.35 g, 70%) was crystallized from ethanol
  10. filtrationThe precipitate was filtered off
  11. customdried in a vacuo

Sources & evidence

ORD record
ord-97c34b6fceb2400cb6294c78a72f8bf3
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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