Methyl pyruvate → HCID 22052052, compound

HRID 1831538Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]1[C:12]([NH2:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[CH3:22])[CH:10]=[CH:9][N:8]=1)[CH3:5].[C:23](OC)(=[O:27])[C:24]([CH3:26])=O>>[CH3:1][O:2][CH2:3][CH:4]([N:6]1[C:23](=[O:27])[C:24]([CH3:26])=[N:13][C:12]2[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=3[CH3:22])=[CH:10][CH:9]=[N:8][C:7]1=2)[CH3:5]

Participants

Reactant 2

HCID 11748Methyl pyruvate

HCID 86591988HCID 86591988, compound

Product 1

HCID 22052052HCID 22052052, compound

Procedure

N2-(2-Methoxy-1-methyl-ethyl)-4-(4-methoxy-2-methyl-phenyl)-pyridine-2,3-diamine (0.066 g, 0.22 mmol) and methyl pyruvate (79 μL, 0.88 mmol) were treated substantially as in Part E of Example 67a to give 4-(2-methoxy-1-methyl-ethyl)-8-(4-methoxy-2-methyl-phenyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 73a): 1H NMR (300 MHz, CDCl3): δ 8.49–8.47 (d, 1H, J=4.8 Hz), 7.16–7.12 (m, 2H), 6.86–6.82 (m, 2H), 4.41–4.36 (m, 1H), 3.87 (s, 3H), 3.84–3.80 (m, 2H), 3.34 (s, 3H), 2.48 (s, 3H), 2.12 (s, 3H), 1.62–1.60 (d, 3H, J=6.9 Hz). MS (AP) 354.2 [(M+H)+, 100].

Sources & evidence

ORD record: ord-99e19e0b0bcb4292af25e4c5e26e962f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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