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Potassium Carbonate → HCID 9950805, compound

HRID 496554
Notes
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Reaction equation

HRID 496554 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([C:10]3=[N:9][CH:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:31][C:32]1[N:33]=[N:34][N:35]([CH3:37])[CH:36]=1>CN(C=O)C.O>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[N:12]=[C:13]([O:20][CH2:31][C:32]4[N:33]=[N:34][N:35]([CH3:37])[CH:36]=4)[C:14]4[C:19]([C:10]3=[N:9][CH:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 223215554-(chloromethyl)-1-methyl-1H-1,2,3-triazole hydrochlorideHCID 22321557HCID 22321557, compound

Product 1

HCID 9950805HCID 9950805, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-(5-Methylisoxazol-3-yl)imidazo[2,1-a]phthalazin-6-one (100 mg, 0.375 mmol) was suspended in DMF (5 ml) and sodium hydride (60% dispersion in oil, 33 mg, 0.83 mmol) was added. After stirring at room temperature for 10 minutes potassium carbonate (50 mg, 0.36 mmol) was added, followed by 4-chloromethyl-1-methyl triazole hydrochloride (69 mg, 0.41 mmol). The solution was heated at 80° C. for 4 hours, then cooled and poured into water. The solid product was filtered off and washed with water and hexane. The solid was recrystallised from ethyl acetate/hexane to yield the title compound (83 mg, 62%), 1H NMR (360 MHz, CDCl3) 2.55 (3H, s), 4.11 (3H, s), 5.75 (2H, s), 6.72 (1H, s), 7.67 (1H, t), 7.86 (1H, t), 7.99 (1H, s), 8.17 (2H, d), 8.51 (1H, d); MS+362 [MH]+.

Workup

  1. additionwas added
  2. temperaturecooled
  3. filtrationThe solid product was filtered off
  4. washwashed with water and hexane
  5. customThe solid was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-75a227f680694b44988544ec3f1fe68a
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06946461B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes