Methyl pyruvate → HCID 22052200, compound

HRID 1831561Notes

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 (0.366 g, 0.99 mmol) and methyl pyruvate (178 μL, 1.97 mmol) were treated as in Part F of Example 133 to give 8-(2-chloro-4-difluoromethoxy-phenyl)-4-(1-methoxymethyl-propyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 122b): 1H NMR (300 MHz, CDCl3) δ 8.56–8.51 (m, 1H), 7.33–7.30 (m, 2H), 7.27–7.23 (m, 2H), 6.82–6.33 (t, 1H, J=72.9 Hz), 6.20–6.18, 5.62–5.57 (2m, 1H), 4.38–4.32 (m,1H), 3.93–3.80 (m, 1H), 3.33 (s, 3H), 2.47 (s, 3H), 2.08–2.00 (m, 2H), 0.90–0.88 (t, 3H, J=6.3 Hz). MS (AP) 424.1 [(M+H)+, 100].

Sources & evidence

ORD record: ord-3716f4cdf7484275842ed4464fe8b4d4
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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