5-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazine → HCID 58845166, compound

HRID 2251062Notes

Reaction equation

HRID 2251062 reaction equation
Br[C:2]1[C:3](=[O:15])[N:4]([C@@H:9]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Br: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]([CH2:12][O:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Br: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 184528095-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazineHCID 692205703,5-dibromo-1-[(1R)-1-(methoxymethyl)propyl]2(1H)-pyrazinone

Product 1

HCID 58845166HCID 58845166, compound

Procedure

Prepared in a similar fashion as described for Example 556 using 3,5-dibromo-1-[(1R)-1-(methoxymethyl)propyl]-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 7.14 (s, 1H), 6.75 (d, J=2.5 Hz, 1H), 6.46 (d, J=2.5 Hz, 1H), 5.08-4.86 (m, 1H), 4.50-3.88 (m, 4H), 3.77 (s, 3H), 3.70-3.52 (m, 2H), 3.36 (s, 3H), 1.92-1.70 (m, 2H), 0.93 (t, J=7.5 Hz, 3H); HRMS (ESI) m/z 501.9992 [(M+H)+, calcd for C18H22N3O4Br2 501.9977].

Workup

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

Sources & evidence

ORD record
ord-a81999de1abd434d8f109f9c520588e6
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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