1-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → 5-chloro-1-[(1R)-1-cyclopropylpropyl]-3-(7-methoxy-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-2(1H)-pyrazinone

HRID 1271197Notes

Reaction equation

HRID 1271197 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4]([C@@H:9]([CH:12]2[CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1.[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]2[NH:22][CH2:23][CH2:24][O:25][C:20]=2[CH:19]=1>>[Cl:8][C:6]1[N:7]=[C:2]([N:22]2[C:21]3[CH:26]=[CH:27][C:18]([O:17][CH3:16])=[CH:19][C:20]=3[O:25][CH2:24][CH2:23]2)[C:3](=[O:15])[N:4]([C@@H:9]([CH:12]2[CH2:14][CH2:13]2)[CH2:10][CH3:11])[CH:5]=1

Participants

3

Reactant 2

HCID 184527991-[(1R)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 198950027-methoxy-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 101340805-chloro-1-[(1R)-1-cyclopropylpropyl]-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 556 using 3,5-dichloro-1-[(1R)-1-cyclopropylpropyl]-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 6.98 (s, 1H), 6.94 (d, J=9.6 Hz, 1H), 6.44–6.41 (m, 2H), 4.33–4.30 (m, 2H), 4.18–4.08 (m, 3H), 3.75 (s, 3H), 1.92–1.78 (m, 2H), 1.10–1.00 (m, 1H), 0.95 (t, J=7.3 Hz, 3H), 0.81–0.77 (m, 1H), 0.60–0.48 (m, 2H), 0.38–0.20 (m, 1H); HRMS (ESI) m/z 376.1452 [(M+H)+, calcd for C19H23N3O3Cl 376.1428].

Workup

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

Sources & evidence

ORD record
ord-54de946b967f47b49bb4f0efc936ca9d
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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