Methyl pyruvate → HCID 22052158, compound

HRID 1831558Notes

Reaction equation

HRID 1831558 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]([CH:23]2[CH2:25][CH2:24]2)[CH2:20][CH2:21][CH3:22])[C:13]=1[NH2:26].[C:27](OC)(=[O:31])[C:28]([CH3:30])=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:26]=[C:28]([CH3:30])[C:27](=[O:31])[N:18]([CH:19]([CH:23]3[CH2:25][CH2:24]3)[CH2:20][CH2:21][CH3:22])[C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 11748Methyl pyruvateHCID 69657899HCID 69657899, compound

Product 1

HCID 22052158HCID 22052158, compound

Procedure

4-(2-Chloro-4-difluoromethoxy-phenyl)-N2-(1-cyclopropyl-butyl)-pyridine-2,3-diamine (0.300 g, 0.79 mmol) and methyl pyruvate (142 μL, 1.58 mmol) were treated substantially as described in Part F of Example 113 to give 8-(2-chloro-4-difluoromethoxy-phenyl)-4-(1-cyclopropyl-butyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 117). 1H NMR (300 MHz, CDCl3) δ 8.47–8.46 (2d, 1H, J=4.8 Hz), 7.37–7.28 (m, 2H), 7.20–7.10 (m, 2H), 6.85–6.37 (t, 1H, J=72.8 Hz), 5.18–5.02, 4.60–4.51 (2m, 1H), 2.49 (s, 3H), 2.40–2.32 (m, 1H), 2.29–2.17 (m, 2H), 2.10–2.00 (m, 1H), 0.92–0.88 (t, 3H, J=7.4 Hz), 0.87–0.77 (m, 1H), 0.59–0.42 (m, 2H), 0.40–0.31 (m, 2H). MS (AP) m/z 434.1 [(M+H)+, 100)].

Sources & evidence

ORD record
ord-193a73653a4944dd9efaee88f5ddfb29
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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