4-(2-(1-Methylpyrrolidin-2-yl)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one → 7-Amino-4-(2-(1-methylpyrrolidin-2-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one
Reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH2:13][O:12][C:11]2[CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=[CH:19][C:10]1=2>C(O)C.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:10]2[N:9]([CH2:8][CH2:7][CH:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])[C:14](=[O:15])[CH2:13][O:12][C:11]=2[CH:16]=1Participants
Procedure
A solution of 4-(2-(1-methylpyrrolidin-2-yl)ethyl)-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (0.49 g, 1.604 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The flask was evacuated and purged twice with hydrogen gas. The reaction stirred at room temperature under hydrogen atmosphere (balloon pressure) for 2 hours. The reaction was filtered through a Celite bed and washed with methanol (3×10 mL). The combined organic layers were evaporated to obtain the crude title compound (0.44 g, quantitative) as a solid. 1H NMR (DMSO-d6) δ 1.39-1.51 (m, 2H), 1.56-1.66 (m, 2H), 1.76-2.06 (m, 4H), 2.16 (s, 3H), 2.88-2.94 (m, 1H), 3.74-3.86 (m, 2H), 4.46 (s, 2H), 5.01 (s, 2H), 6.22 (d, 1H, J=2.4 Hz), 6.26 (dd, 1H, J=2.1, 8.4 Hz), 6.82 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %): 276 (MH+, 100).
Workup
- custompurged with hydrogen gas
- customThe flask was evacuated
- custompurged twice with hydrogen gas
- filtrationThe reaction was filtered through a Celite bed
- washwashed with methanol (3×10 mL)
- customThe combined organic layers were evaporated
Sources & evidence
- ORD record
- ord-3ad4bcc67755468cbccfba4f5bc9940d
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618286B2
Reaction notes
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