3,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone → 5-chloro-1-(1-cyclobutylpropyl)-3-(7-methoxy-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-2(1H)-pyrazinone

HRID 1271196Notes

Reaction equation

HRID 1271196 reaction equation
Cl[C:2]1[C:3](=[O:16])[N:4]([CH:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:17][O:18][C:19]1[CH:28]=[CH:27][C:22]2[NH:23][CH2:24][CH2:25][O:26][C:21]=2[CH:20]=1>>[Cl:8][C:6]1[N:7]=[C:2]([N:23]2[C:22]3[CH:27]=[CH:28][C:19]([O:18][CH3:17])=[CH:20][C:21]=3[O:26][CH2:25][CH2:24]2)[C:3](=[O:16])[N:4]([CH:9]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 184527943,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinoneHCID 198950027-methoxy-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 102003765-chloro-1-(1-cyclobutylpropyl)-3-(7-methoxy-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-2(1H)-pyrazinone

Procedure

Prepared in a similar fashion as described for Example aaa using 3,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone and 7-methoxy-3,4-dihydro-2H-1,4-benzoxazine as the starting materials to give an oil. 1H NMR (300 MHz, CDCl3) δ 6.91 (d, J=9.5 Hz, 1H), 6.69 (s, 1H), 6.46–6.41 (m, 2H), 4.92–4.82 (m, 1H), 4.34–4.31 (m, 2H), 4.20–4.16 (m, 2H), 3.76 (s, 3H), 2.64–2.50 (m, 1H), 2.24–2.12 (m, 1H), 1.96–1.40 (m, 7H), 0.84 (t, J=7.5 Hz, 3H); HRMS (ESI) m/z 390.1595 [(M+H)+, calcd for C20H25N3O3Cl 390.1584].

Workup

  1. customPrepared in a similar fashion
  2. customto give an oil

Sources & evidence

ORD record
ord-160a8f54163c4ad39ccdcaaff64cceb5
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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