Ammonium → HCID 66621374, compound

HRID 415341Notes

Reaction equation

HRID 415341 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[O:18][C:19]3[C:25]([C:26]([O:28]C)=O)=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+:30]>CO>[C:26]([C:25]1[C:19]2[O:18][C:17]([CH:14]3[CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])[CH2:16][CH2:15]3)=[N:21][C:20]=2[CH:22]=[CH:23][CH:24]=1)(=[O:28])[NH2:30]

Participants

4

Reactant 2

HCID 223AmmoniumHCID 66621319HCID 66621319, compound

Product 1

HCID 66621374HCID 66621374, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-(benzyloxycarbonyl)piperidin-4-yl)benzo[d]oxazole-7-carboxylate (560 mg, 1.4 mmol) was added to a solution of ammonium in methanol (10 mL) in a sealing tube and the mixture was stirred at room temperature for 2 days. The resulting mixture was evaporated and the crude product was purified by prep-HPLC to give benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (200 mg, yield 37%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.94-1.98 (m, 2H), 2.18-2.22 (m, 2H), 3.06-3.12 (m, 2H), 3.20-3.23 (m, 1H), 4.26 (brs, 2H), 5.16 (s, 2H), 6.30 (s, 1H), 6.92 (s, 1H), 7.32-7.38 (m, 5H), 7.42-7.46 (t, J=8.0 Hz, 1H), 7.84-7.87 (dd, J1=8.0 Hz, J2=1.2 Hz, 1H), 8.06-8.08 (dd, J1=8.0 Hz, J2=1.2 Hz, 1H); LC-MS (ESI) m/z: 380 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated
  2. customthe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-c8529fe67c514972a64469acf0877218
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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