Methyl pyruvate → HCID 22052200, compound

HRID 1831560Notes

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]([CH2:22][O:23][CH3:24])[CH2:20][CH3:21])[C:13]=1[NH2:25].[C:26](OC)(=[O:30])[C:27]([CH3:29])=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:25]=[C:27]([CH3:29])[C:26](=[O:30])[N:18]([CH:19]([CH2:22][O:23][CH3:24])[CH2:20][CH3:21])[C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

Reactant 2

HCID 11748Methyl pyruvate

HCID 69658630HCID 69658630, compound

Product 1

HCID 22052200HCID 22052200, compound

Procedure

4-(2-Chloro-4-difluoromethoxy-phenyl)-N2-(1-methoxymethyl-propyl)-pyridine-2,3-diamine (0.268 g, 0.72 mmol) and methyl pyruvate (130 μL, 1.44 mmol) were treated substantially as described in Part F of Example 113 to give 8-(2-chloro-4-difluoromethoxy-phenyl)-4-(1-methoxymethyl-propyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 122a): 1H NMR (300 MHz, CDCl3) δ □8.54–8.51 (m, 1H), 7.33–7.32 (m,2H), 7.21–7.14 (m, 2H), 6.85–6.37 (t, 1H, J=72.9 Hz), 6.21–6.19, 5.64–5.58 (2m, 1H), 4.40–4.31 (m, 1H), 3.92–3.79 (m, 1H), 3.33 (s, 3H), 2.48 (s, 3H), 2.30–2.20 (m, 1H),2.13–1.96 (m, 1H), 0.90–0.85 (t, 3H, J=7.7 Hz). MS (AP) m/z 424.1 [(M+H)+, 100].

Sources & evidence

ORD record: ord-30d0c1e049b941f7b1f3989b17472a3e
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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