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

HRID 1788055Notes

Reaction equation

HRID 1788055 reaction equation
[BH4-].[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]([O:34][CH3:35])=[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:36]=[N:37][N:38]=[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]([O:34][CH3:35])=[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:36]=[N:37][N:38]=[C:12]3[NH:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 688609185-(3-chlorophenyl)-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol

Product 1

HCID 1363420825-(3-chlorophenyl)-4,5-dihydro-alpha-(4-methoxyphenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanolYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.003 mol) was added portionwise at room temperature to a mixture of intermediate 16 (0.003 mol) in methanol (15 ml). The mixture was stirred at room temperature for 2 hours and poured out into ice water. DCM was added. The mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (1.3 g, 86%) was crystallized from 2-propanone/diethyl ether. The precipitate was filtered off and dried, yielding 1 g (67%) of 5-(3-chlorophenyl)-4,5-dihydro-α-(4-methoxyphenyl)-α-(1-methyl-1H-imidazol-5-yl)-tetrazolo[1,5-a]quinazoline-7-methanol (intermediate 17), mp. 220° C.

Workup

  1. extractionThe mixture was extracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (1.3 g, 86%) was crystallized from 2-propanone/diethyl ether
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-4dfd5f10146d40e5832362af6c04be9c
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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