Ammonia → HCID 66621425, compound

HRID 415327Notes

Reaction equation

HRID 415327 reaction equation
[N:1]12[CH2:8][C:5]([C:9]3[O:10][C:11]4[C:17]([C:18]([O:20]C)=O)=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[NH3:22]>CO>[N:1]12[CH2:8][C:5]([C:9]3[O:10][C:11]4[C:17]([C:18]([NH2:22])=[O:20])=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 222AmmoniaHCID 66621155HCID 66621155, compound

Product 1

HCID 66621425HCID 66621425, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-azabicyclo[3.2.1]octan-5-yl)benzo[d]oxazole-7-carboxylate (80 mg, 0.28 mmol) was added to ammonia in methanol (15 ml) and the mixture was stirred at room temperature for 3 days. Then the solid was filtered, washed with methanol, the residue solution was concentrated under vacuum. Then the residue was purified by flash column chromatography to give 2-(1-azabicyclo[3.2.1]octan-5-yl)benzo[d]oxazole-7-carboxamide (20.6 mg, yield: 27%) 1H-NMR (400 MHz, CD3OD) δ: 1.18 (s, 1H), 1.63-1.67 (m, 1H), 1.82 (s, 1H), 1.94-1.98 (m, 1H), 2.10-2.15 (m, 2H), 2.23-2.28 (m, 1H), 2.38-2.44 (m, 1H), 2.91-2.93 (m, 2H), 3.12-3.18 (m, 1H), 3.20-3.30 (m, 1H), 7.34-7.37 (t, J=8 Hz, 1H), 7.72-7.77 (m, 2H), LC-MS (m/z): 272 (M+1)+.

Workup

  1. filtrationThen the solid was filtered
  2. washwashed with methanol
  3. concentrationthe residue solution was concentrated under vacuum
  4. customThen the residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-880e1151f55743d4969117ccce860466
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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