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

HRID 1788066Notes

Reaction equation

HRID 1788066 reaction equation
[B-].[Na+].O.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)[NH2:22])[CH:19]=3)[N:14]3[N:36]=[N:37][N:38]=[C:13]3[N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(Cl)Cl>CO>[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([C:30]4[N:34]([CH3:35])[CH:33]=[N:32][CH:31]=4)([C:23]4[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=4)[NH2:22])[CH:19]=3)[N:14]3[N:36]=[N:37][N:38]=[C:13]3[NH:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 22959485VertellusHCID 688609215-(3-chlorophenyl)-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine hydrate

Product 1

HCID 1363420835-(3-chlorophenyl)-4,5-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamineYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroborate (0.0005 mol) was added portionwise at room temperature to a mixture of intermediate 27 (0.0005 mol) in methanol (2.5 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, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over kromasil® (5 μm) (eluent: DCM/MeOH/Et3N 97/3/0.3). The pure fractions were collected and the solvent was evaporated. The residue (0.1 g, 40%) was taken up in diethyl ether and dried in a vacuo, yielding 0.07 g (28%) of 5-(3-chlorophenyl)-4,5-dihydro-α-(1-methyl-1H-imidazol-5-yl)-α-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine (intermediate 28), mp. 140° C.

Workup

  1. extractionThe mixture was extracted with DCM
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over kromasil® (5 μm) (eluent: DCM/MeOH/Et3N 97/3/0.3)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customdried in a vacuo

Sources & evidence

ORD record
ord-8deae60c94284616a589f5ea5b9930c6
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

Loading…