3,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone → HCID 10140009, compound

HRID 1271193Notes

Reaction equation

HRID 1271193 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.[Br:17][C:18]1[C:23]2[NH:24][CH2:25][CH2:26][O:27][C:22]=2[CH:21]=[C:20]([O:28][CH3:29])[CH:19]=1>>[Br:17][C:18]1[C:23]2[N:24]([C:2]3[C:3](=[O:16])[N:4]([CH:9]([CH:12]4[CH2:15][CH2:14][CH2:13]4)[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=3)[CH2:25][CH2:26][O:27][C:22]=2[CH:21]=[C:20]([O:28][CH3:29])[CH:19]=1

Participants

3

Reactant 2

HCID 184527943,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinoneHCID 184528095-Bromo-3,4-dihydro-7-methoxy-2H-1,4-benzoxazine

Product 1

HCID 10140009HCID 10140009, compound

Procedure

Prepared in a similar fashion as described for Example 556 using 3,5-dichloro-1-(1-cyclobutylpropyl)-2(1H)-pyrazinone and 5-bromo-7-methoxy-3,4-dihydro-2H-1,4-benzoxazine as the starting materials to give a brown oil. 1H NMR (300 MHz, CDCl3): δ 6.73 (d, J=2.9 Hz, 1H), 6.72 (s, 1H), 6.45 (d, J=2.6 Hz, 1H), 4.90–4.85 (m, 1H), 4.50–3.88 (m, 4H), 3.76 (s, 3H), 2.58–2.50 (m, 1H), 2.18–2.13 (m, 1H), 1.85–1.65 (m, 6H), 1.50–1.40 (m, 1H), 0.83 (t, J=7.4 Hz, 3H), HRMS (ESI) m/z 468.0665 [M+, calcd for C20H24N3O3BrCl 468.0690].

Workup

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

Sources & evidence

ORD record
ord-b6554ba9e311440583b79be59f6e48e1
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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