Diisobutylaluminumhydride → 1-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[N+:11]([C:14]1[C:19]2[NH:20][C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)([C:24]#[N:25])[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]>C1(C)C=CC=CC=1>[N+:11]([C:14]1[C:19]2[NH:20][C:21]([CH2:24][NH2:25])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH2:22][O:23][C:18]=2[CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]Participants
4
Procedure
1.0 M Diisobutylaluminum hydride in toluene (200 μL, 0.2 mmol) was added drop-wise to a solution of 5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazine-3-carbonitrile (50 mg, 0.2 mmol) (Example 71, Step 1), in toluene (5 mL) at room temperature. The reaction mixture was stirred for 10 min, then quenched with methanol. The resulting mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give crude 1-(5-nitro-3-pyridin-2-yl-3,4-dihydro-2H-1,4-benzoxazin-3-yl)methanamine solid (0.05 g. 100%). LCMS calculated for C14H15N4O3 (M+H)+: m/z=287.1. found: 287.1.
Workup
- customat room temperature
- customquenched with methanol
- customThe resulting mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
- washThe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ba434527723b4290979392eaecd9c460
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227985B2
Reaction notes
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