Ethanolamine → 8-{2-[2-(4-bromophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

HRID 12120Notes

Reaction equation

HRID 12120 reaction equation
C(CN)O.C([O:12][C:13]1[CH:14]=[C:15]([C:24](=[O:28])[CH:25](O)O)[C:16]2[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=2[CH:23]=1)C1C=CC=CC=1.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1>>[Br:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][C:37]([NH:40][CH2:25][CH:24]([C:15]2[C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=[C:13]([OH:12])[CH:14]=2)[OH:28])([CH3:38])[CH3:39])=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 738391-(4-Bromophenyl)-2-methylpropan-2-amineHCID 220634476-benzyloxy-8-(2,2-dihydroxyacetyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 115393488-{2-[2-(4-bromophenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-6-hydroxy-4H-benzo[1,4]oxazin-3-one

Procedure

The preparation of the ethanolamine and debenzylation were carried out as described in Example 19 from 300 mg (0.91 mmol) of 6-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 250 mg (1.09 mmol) of 2-(4-bromophenyl)-1,1-dimethylethylamine. Beige solid. Yield: 54 mg (14%); mass spectrometry: [M+H]+=435, 437.

Sources & evidence

ORD record
ord-07cf27db35be458b8df1e8c9dafe6b6e
Source dataset
uspto-grants-2010_06
Patent number
US07727984B2

Reaction notes

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