5-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazine → HCID 10182040, compound

HRID 1271195Notes

Reaction equation

HRID 1271195 reaction equation
Cl[C:2]1[C:3](=[O:14])[N:4]([C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:5]=[C:6]([Cl:8])[N:7]=1.[Br:15][C:16]1[C:21]2[NH:22][CH2:23][CH2:24][O:25][C:20]=2[CH:19]=[C:18]([O:26][CH3:27])[CH:17]=1>>[Br:15][C:16]1[C:21]2[N:22]([C:2]3[C:3](=[O:14])[N:4]([C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:5]=[C:6]([Cl:8])[N:7]=3)[CH2:23][CH2:24][O:25][C:20]=2[CH:19]=[C:18]([O:26][CH3:27])[CH:17]=1

Participants

3

Reactant 2

HCID 184528095-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazineHCID 44189862HCID 44189862, compound

Product 1

HCID 10182040HCID 10182040, compound

Procedure

Prepared in a similar fashion as described for Example 556 using 3,5-dichloro-1-[(1S)-2-methoxy-1-methylethyl]-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 7.06 (s, 1H), 6.74 (d, J=3.0 Hz, 1H), 6.45 (d, J=2.5 Hz, 1H), 5.24–5.10 (m, 1H), 4.52–3.86 (m, 4H), 3.76 (s, 3H), 3.57 (d, J=3.7 Hz, 2H), 3.35 (s, 3H), 1.41 (d, J=6.9 Hz, 3H); HRMS (ESI) m/z 444.0339 [(M+H)+, calcd for C17H20N3O4BrCl 444.0326].

Workup

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

Sources & evidence

ORD record
ord-f46ba24ca8014719bbb77caf16ac4299
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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