(1-Methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate → (1-Methylazetidin-3-yl)methyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate

HRID 2201689Notes

Reaction equation

HRID 2201689 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:24])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([CH3:23])[CH2:20]1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16](=[O:24])[O:17][CH2:18][CH:19]1[CH2:22][N:21]([CH3:23])[CH2:20]1

Participants

4

Reactant 1

HCID 71007324(1-Methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 71465771(1-Methylazetidin-3-yl)methyl (2-amino-5-(thiophen-2-yl)phenyl)carbamateYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (1-methylazetidin-3-yl)methyl (2-nitro-5-(thiophen-2-yl)phenyl)carbamate (0.06 g, 0.16 mmol, 1 eq.) in MeOH (5 mL) was added Pd/C (0.03 g, 0.24 mmol, 1.5 eq). The reaction was stirred at room temperature under H2 atmosphere for 2 h. The reaction mixture was filtered through Celite and concentrated. The crude solid, which was washed with ether and pentane to obtain (1-methylazetidin-3-yl)methyl (2-amino-5-(thiophen-2-yl)phenyl)carbamate (0.03 g, 62% yield) as ash color solid. ESI+ MS: m/z 318 ([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 8.69 (bs, 1H), 7.50 (bs, 1H), 7.34 (d, J=4.5 Hz, 1H), 7.22-7.16 (m, 2H), 7.06-7.02 (m, 1H), 6.72 (d, J=8.0 Hz, 1H), 5.13 (bs, 2H), 4.19 (d, J=6.5 Hz, 2H), 3.54-3.45 (m, 2H), 3.25-3.15 (m, 2H), 2.82-2.70 (m, 1H), 2.35 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. washThe crude solid, which was washed with ether and pentane

Sources & evidence

ORD record
ord-09793c3d96ca4e84bd385b8635136513
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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