Methyl pyruvate → HCID 22052075, compound

HRID 1831554Notes

Reaction equation

HRID 1831554 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:22]2[CH2:24][CH2:23]2)[CH2:20][CH3:21])[C:13]=1[NH2:25].[C:26](OC)(=[O:30])[C:27]([CH3:29])=O>C(O)C>[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]([CH:22]3[CH2:24][CH2:23]3)[CH2:20][CH3:21])[C:14]=2[N:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 11748Methyl pyruvateHCID 69658011HCID 69658011, compound

Product 1

HCID 22052075HCID 22052075, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-chloro-4-difluoromethoxy-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine (0.088 g, 0.24 mmol) and methyl pyruvate (140 μL, 1.54 mmol) were treated as in Part F of Example 113 with the exception that ethanol was used as the solvent, gave 8-(2-Chloro-4-difluoromethoxy-phenyl)-4-(1-cyclopropyl-propyl)2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 115a): 1H NMR (300 MHz, CDCl3) δ 8.48–8.46 (2d, 1H, J=4.7 Hz), 7.37–7.33 (m, 2H), 7.19–7.14 (m, 2H), 6.86–6.37 (t,1H, J=73.3 Hz), 5.16–4.92, 4.90–4.41 (2m, 1H), 2.57 (s, 3H), 2.49–2.38 (m, 1H), 2.29–2.19 (m, 1H), 2.10–1.93 (m, 1H), 0.90–0.85 (t, 3H, J=7.3), 0.80–0.71 (m, 1H), 0.59–0.50 (m, 1H), 0.49–0.48 (m, 1H), 0.23–0.18 (m, 1H). MS (AP) m/z 420.1 [(M+H)+, 100].

Sources & evidence

ORD record
ord-14040decdb844f129fa832b26f3d33ca
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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