4-Chlorophenylglyoxylic acid → 2-(4-chlorophenyl)-4-cyclopropylmethylpyrido[2,3-b]pyrazin-3(4H)-one

HRID 1913082

Reaction equation

HRID 1913082 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[C:21](O)=[O:22])=[CH:16][CH:15]=1>C=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:22])[N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 1459984-Chlorophenylglyoxylic acidHCID 28902457N2-(cyclopropylmethyl)pyridine-2,3-diamine

Product 1

HCID 442184372-(4-chlorophenyl)-4-cyclopropylmethylpyrido[2,3-b]pyrazin-3(4H)-oneYield 36.6%

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

430 mg (2.63 mM) of N2-(cyclopropylmethyl)pyridine-2,3-diamine and 485.4 mg (2.63 mM) of (4-chlorophenyl)(oxo)acetic acid in 6 ml of methanal were refluxed for 16 h. A solid crystallized. The compound was filtered and washed with methanol to give 300 mg of 2-(4-chlorophenyl)-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one as a beige solid. Yield: 36.5%.

Workup

  1. customA solid crystallized
  2. filtrationThe compound was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-5734a1bdf3c34a22b64aa6fdd58cbc5f
Source dataset
uspto-grants-2013_12
Patent number
US08609689B2

Linked notes

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