Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylate → 2-(Azetidin-3-yl)benzo[d]oxazole-7-carboxamide

HRID 415261Notes

Reaction equation

HRID 415261 reaction equation
[C:1]([C:4]1[C:12]2[O:11][C:10]([CH:13]3[CH2:16][N:15](C(OCC4C=CC=CC=4)=O)[CH2:14]3)=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2]>[Pd].CO>[NH:15]1[CH2:14][CH:13]([C:10]2[O:11][C:12]3[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=[CH:7][C:8]=3[N:9]=2)[CH2:16]1

Participants

4

Reactant 1

HCID 66621201Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylate

Product 1

HCID 666214382-(Azetidin-3-yl)benzo[d]oxazole-7-carboxamideYield 6.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)azetidine-1-carboxylate (160 mg, 0.45 mmol), 10% Pd/C (20 mg) of methanol (30 ml) was stirred at room temperature for 2 h. Then the mixture was filtered and evaporated under reduced pressure. The residue was purified by pre-HPLC. 6 mg of 2-(azetidin-3-yl)benzo[d]oxazole-7-carboxamide was obtained. LC-MS (ESI) m/z: 218 (M+1)+. 1H-NMR (400 MHz, CDCl3): δ 1.84 (brs, 1H), 3.39 (t, 3H), 4.11 (t, 3H), 4.21 (m, 1H), 6.12 (brs, 1H), 6.96 (brs, 1H), 7.39 (t, J=8 Hz, 1H), 7.81 (d, J=8 Hz, 1H), 8.01 (d, J=8 Hz, 1H).

Workup

  1. filtrationThen the mixture was filtered
  2. customevaporated under reduced pressure
  3. customThe residue was purified by pre-HPLC

Sources & evidence

ORD record
ord-d8357b5fdf7b4ad8b6b9b27f37490d51
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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