Phthalic Anhydride → HCID 135964510, compound

HRID 1046820Notes

Reaction equation

HRID 1046820 reaction equation
[NH2:1][C:2]1[N:25]=[C:5]2[NH:6][C:7]([CH3:24])=[C:8]([C:22]#[N:23])[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][C:11]=3[S:18]([CH3:21])(=[O:20])=[O:19])[N:4]2[N:3]=1.[C:26]1(=O)[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.C(N(CC)CC)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[N:4]3[N:3]=[C:2]([N:1]4[C:29](=[O:30])[C:28]5[C:27](=[CH:35][CH:34]=[CH:33][CH:32]=5)[C:26]4=[O:31])[N:25]=[C:5]3[NH:6][C:7]([CH3:24])=[C:8]2[C:22]#[N:23])=[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:12]=1)#[N:17]

Participants

6

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 136355666HCID 136355666, compound

Product 1

HCID 135964510HCID 135964510, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

Under argon, (rac)-2-amino-7-[4-cyano-2-(methylsulfonyl)phenyl]-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (60 mg, 0.17 mmol) together with phthalic anhydride (50.02 mg, 0.34 mmol, 2.0 eq.) was suspended in a mixture of toluene (4 ml) and pyridine (2 ml), triethylamine (4.7 μl, 0.034 mmol, 0.2 eq.) was added and the mixture was heated under reflux for 2 h. The reaction mixture was then concentrated under reduced pressure. From the residue, the product was precipitated by addition of ethanol (2 ml) in an ultrasonic bath. The precipitate was filtered off and dried under high vacuum. This gave 67 mg (75.6% of theory) of the title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 h
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. customFrom the residue, the product was precipitated by addition of ethanol (2 ml) in an ultrasonic bath
  6. filtrationThe precipitate was filtered off
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-940a10bb71cf4155adab775d6a810ba1
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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