1-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinone → HCID 10297912, compound

HRID 2251059Notes

Reaction equation

HRID 2251059 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.[Br:16][C:17]1[C:22]2[NH:23][CH2:24][CH2:25][O:26][C:21]=2[CH:20]=[C:19]([O:27][CH3:28])[CH:18]=1>>[Br:16][C:17]1[C:22]2[N:23]([C:2]3[C:3](=[O:15])[N:4]([C@H:9]([CH:12]4[CH2:14][CH2:13]4)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=3)[CH2:24][CH2:25][O:26][C:21]=2[CH:20]=[C:19]([O:27][CH3:28])[CH:18]=1

Participants

3

Reactant 2

HCID 184528011-[(1S)-1-cyclopropylpropyl]-3,5-dichloro-2(1H)-pyrazinoneHCID 184528095-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazine

Product 1

HCID 10297912HCID 10297912, compound

Procedure

Prepared in a similar fashion as described for Example 556 using 3,5-dichloro-1-[(1S)-1-cyclopropylpropyl]-2(1H)-pyrazinone and 5-bromo-7-methoxy-3,4-dihydro-2H-1,4-benzoxazine as the starting materials to give an oil. 1H NMR (300 MHz, CDCl3): δ 7.03 (s, 1H), 6.73 (d, J=2.9 Hz, 1H), 6.45 (d, J=2.9 Hz, 1H), 4.44-3.89 (m, 5H), 3.75 (s, 3H), 1.96-1.70 (m, 2H), 1.12-1.00 (m, 1H), 0.92 (t, J=7.3 Hz, 3H), 0.92 (t, J=7.3 Hz, 3H), 0.84-0.72 (m, 1H), 0.56-0.44 (m, 2H), 0.35-0.25 (m, 1H); HRMS (ESI) m/z 454.0518 [(M+H)+, calcd for C19H22N3O3BrCl 454.0533].

Workup

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

Sources & evidence

ORD record
ord-efb602ec861f4e2a9ced539fe6440459
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

Loading…