Methyl pyruvate → HCID 22052142, compound

HRID 1831559Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[C:13]=1[NH2:24].[C:25](OC)(=[O:29])[C:26]([CH3:28])=O>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]2[N:24]=[C:26]([CH3:28])[C:25](=[O:29])[N:18]([CH:19]([CH3:23])[CH2:20][O:21][CH3:22])[C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 11748Methyl pyruvate

HCID 69658108HCID 69658108, compound

Product 1

HCID 22052142HCID 22052142, compound

Procedure

4-(2-Chloro-4-difluoromethoxy-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine (0.149 g, 0.42 mmol) and methyl pyruvate (75 μL, 0.83 mmol) were treated substantially as described in Part F of Example 113 to give 8-(2-chloro-4-difluoromethoxy-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 121a): 1H NMR (300 MHz, CDCl3): δ 8.54–8.53 (d, 1H, J=4.8 Hz), 7.34–7.32 (m, 2H), 7.21–7.13 (m, 2H), 6.85–6.36 (t, 1H, J=73.2 Hz), 4.41–4.37 (m, 1H), 3.82–3.76 (m, 2H), 3.34 (s, 3H), 2.47 (s, 3H), 1.62 (d, 3H, J=6.9 Hz). MS (AP) m/z 410.0 [(M+H)+, 100].

Sources & evidence

ORD record: ord-c7ad8f84549d4f72a0cbf8f66adb79af
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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