Diethyl Ether → HCID 178488912, compound

HRID 1526121Notes

Reaction equation

HRID 1526121 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:10](=[O:19])[O:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=O)=[CH:5][CH:4]=1.[NH2:22][C:23]1[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=1.C([O-])(=O)C.[NH4+].C(OCC)C>C(O)(=O)C.CO>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]2[N:22]=[C:23]3[NH:24][N:25]=[C:26]([CH3:28])[C:27]3=[C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[O:11][C:10](=[O:19])[C:9]=23)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 517165Ammonium AcetateHCID 127770683-(4-Methoxybenzoyl)-2H-1-benzopyran-2-one

Product 1

HCID 178488912HCID 178488912, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2.1 g (7.49 mmol) of 3-(4-methoxybenzoyl)-2H-chromen-2-one with 728 mg (7.49 mmol) of 3-amino-5-methyl-pyrazole in 15 ml of acetic acid is heated at 110° C. for 10 minutes. 2.3 g (30 mmol) of ammonium acetate is then added and then the mixture is carried at 150° C. for 3 h. The solution is placed at room temperature and then 30 ml of ethyl ether and 5 ml of methanol are added. The white solid formed is filtered and then rinsed with diethyl ether to yield 810 mg of 5-(4-methoxyphenyl)-1-methylchromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one.

Workup

  1. customis placed at room temperature
  2. customThe white solid formed
  3. filtrationis filtered
  4. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-d27bb8b7721e445f94fd87c4bdec5463
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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