Water → [3-(4-Methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-[3-(2H-tetrazol-5-yl)-phenyl]-amine

HRID 424403Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[N:14]=[C:15]([NH:22][C:23]4[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=4)[C:26]#[N:27])[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:5][CH:4]=1.[N-:31]=[N+:32]=[N-:33].[Na+].Cl.C(N(CC)CC)C.O>CN1CCCC1=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]3[N:14]=[C:15]([NH:22][C:23]4[CH:30]=[CH:29][CH:28]=[C:25]([C:26]5[N:31]=[N:32][NH:33][N:27]=5)[CH:24]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 3-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-ylamino]-benzonitrile (compound T1) (5.0 g, 12.7 mmol) in N-methylpyrrolidinone (80 mL) are added sodium azide (2.90 g, 44.6 mmol) and triethyl amine hydrochloride (6.14 g, 44.6 mmol). The mixture is stirred at 100° C. for 2 days. Upon cooling, water (400 mL) is added to the reaction mixture and the resulting precipitate is filtered. The solid is washed successively with MeOH, AcOEt, a saturated solution of NH4Cl and water. The residue is dried azeotropically with toluene to yield 2.97 g (54%) of the title compound as light brown solid.

Workup

temperatureUpon cooling
filtrationthe resulting precipitate is filtered
washThe solid is washed successively with MeOH, AcOEt
dry with materialThe residue is dried azeotropically with toluene

Sources & evidence

ORD record: ord-d00d230088ea45478ba40a5ba9cbaf58
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106047B2

Reaction notes

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