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2-Propanol, reaction products with ammonia, distn. residues → 5-(3-Chlorophenyl)-alpha-(1-methyl-1h-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine

HRID 1441475
Notes
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Reaction equation

HRID 1441475 reaction equation
Cl.Cl[C:3]([C:31]1[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=1)([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]1[N:14]=[N:15][N:16]=[C:9]1[N:8]=[C:7]2[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1.[NH3:37].CC(O)C>C1COCC1>[Cl:23][C:19]1[CH:18]=[C:17]([C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:3]([C:31]4[N:35]([CH3:36])[CH:34]=[N:33][CH:32]=4)([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)[NH2:37])[CH:5]=3)[N:10]3[N:14]=[N:15][N:16]=[C:9]3[N:8]=2)[CH:22]=[CH:21][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 1317273757-[chloro(1-methyl-1H-imidazol-5-yl)(4-methylphenyl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinazoline. hydrochloride

Product 1

HCID 686873395-(3-Chlorophenyl)-alpha-(1-methyl-1h-imidazol-5-yl)-alpha-(4-methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamineYield 33%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
5 °C

Procedure

A mixture of intermediate 26 (0.0083 mol) in THF (80 ml) was cooled to 5° C. under N2 flow. NH3/iPrOH (80 ml ) was added dropwise. The mixture was stirred at 5° C. for 1 hours, then brought to room temperature. The mixture was stirred at room temperature overnight, poured out into ice water and 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 silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH 96/4/0.2). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding 1.37 g (33%) of 5-(3-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-α-(4—methylphenyl)-tetrazolo[1,5-a]quinazoline-7-methanamine .hydrate (1:1) (intermediate 27), mp. 150° C.

Workup

  1. custombrought to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH 96/4/0.2)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from CH3CN
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-73dbfff319604bad9649169bd73c0bc6
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07655654B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes