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Ammonium Chloride → HCID 178492824, compound

HRID 238209
Notes
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Reaction equation

HRID 238209 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32]#[N:33])[CH:26]=4)[N:21]=3)[CH3:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:13][CH2:14][N:15]([CH:18]([C:20]3[N:29]([CH3:30])[C:28](=[O:31])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([C:32]5[NH:36][N:35]=[N:34][N:33]=5)[CH:26]=4)[N:21]=3)[CH3:19])[CH2:16][CH2:17]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 599931892-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile

Product 1

HCID 178492824HCID 178492824, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To the 1 ml DMF solution of 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-4-oxo-3,4-dihydro-quinazoline-6-carbonitrile (10.0 mg, 0.02 mmol) was added sodium azide (16.7 mg, 0.24 mmol) and ammonium chloride (12.8 mg, 0.24 mmol). The reaction test tube was flushed with N2 and was irradiated at 200° C. for 40 minutes in the SmithSynthesizer Microwave Reactor with vigorous agitation by a magnetic stirrer. The mixture was cooled to room temperature, the solvent was removed by reduce pressure and extracted with water and ethyl acetate, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3-methyl-6-(1H-tetrazol-5-yl)-3H-quinazolin-4-one (Yield 3.09 mg, 9.8%). 1H NMR (400 MHz, MeOD-d4): δ 1.79 (d, 3H, J=6.57 Hz), 3.39-3.12 (m, 8H), 3.70 (s, 3H), 3.92 (s, 3H), 4.70 (s, br, 1H), 7.17 (d, 2H, J=9.09 Hz), 7.76 (d, 2H, J=9.09 Hz), 7.87 (d, 1H, J=8.59 Hz), 8.47 (dd, 1H, J=8.59, 1.77 Hz), 8.89 (d, 1H, J=1.77 Hz). MS m/z calc. 510.18 found (ESI); 511.4 (M+1)+. Retention time 2.2 minutes.

Workup

  1. customThe reaction test tube was flushed with N2
  2. customwas irradiated at 200° C. for 40 minutes in the SmithSynthesizer Microwave Reactor with vigorous agitation by a magnetic stirrer
  3. customthe solvent was removed
  4. extractionextracted with water and ethyl acetate
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customPurification
  8. customThe product was collected
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ee664f6985c34da5bfbeddca3e721643
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes