Methyl pyruvate → HCID 22052075, compound

HRID 1831557Notes

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>>[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

Reactant 2

HCID 11748Methyl pyruvate

HCID 69658011HCID 69658011, compound

Product 1

HCID 22052075HCID 22052075, compound

Procedure

4-(2-Chloro-4-difluoromethoxy-phenyl)-N2-(1-cyclopropyl-propyl)-pyridine-2,3-diamine (0.284 g, 0.77 mmol) and methyl pyruvate (140 μL, 1.54 mmol) were treated substantially as described in Part F of Example 113 to give 8-(2-Chloro-4-difluoromethoxy-phenyl)-4-(1-cyclopropyl-propyl)2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 115b): 1H NMR (300 MHz, CDCl3) δ 8.52–8.46 (2d, 1H, J=4.8), 7.37–7.32 (m, 2H), 7.26–7.14 (m, 2H), 6.85–6.37(t,1H, J=73.3 Hz), 5.09–4.95, 4.75–4.2 (2m, 1H), 2.48 (s, 3H), 2.4–2.25 (m, 1H), 2.23–2.16 (m, 1H), 2.13–1.93 (m, 1H), 0.90–0.85 (t, 3H, J=7.3 Hz), 0.80–0.67 (m, 1H), 0.57–0.42 (m, 1H), 0.40–0.29 (m, 1H), 0.24–0.18 (m, 1H). MS (AP) m/z 420.2 [(M+H)+, 100], 461.3 [(M+H+CH3CN)+, 20].

Sources & evidence

ORD record: ord-2e37323da826451c80cb3a457b7500e8
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067658B2

Reaction notes

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