Pyridine → HCID 11611121, compound

HRID 969890Notes

Reaction equation

HRID 969890 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([NH2:27])[CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2.N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(Cl)Cl>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([C:12]1[CH:13]=[C:14]([NH:27][C:34](=[O:36])[CH3:35])[CH:15]=[C:16]3[O:20][C:19]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:18][C:17]=13)=[O:11])[CH2:2]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11537818HCID 11537818, compound

Product 1

HCID 11611121HCID 11611121, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-azabicyclo[2.2.2]oct-3-yl)-6-amino-2-phenylbenzoxazole-4-carboxamide (35 mg, 0.09 mmol) in methylene chloride (1 mL) was added pyridine (11 μL, 0.14 mmol) and acetic anhydride (11 μL, 0.10 mmol) at 0° C. and stirred for 30 min, then allowed to warm to room temperature for 1 h. The reaction mixture was quenched with saturated solution of sodium bicarbonate and concentrated under reduced pressure. The crude was purified by semi-preparative HPLC to afford N-(1-azabicyclo[2.2.2]oct-3-yl)-6-acetylamino-2-phenylbenzoxazole-4-carboxamide (13 mg, 44%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.58 (d, J=7.4 Hz, 1H), 8.73 (d, J=1.9 Hz, 1H), 8.20 (d, J=6.8 Hz, 1H), 8.13 (s, 1H), 7.81 (d, J=1.7 Hz, 1H), 7.55-7.50 (m, 4H), 4.35-4.27 (m, 1H), 3.57-3.48 (m, 1H), 3.16-3.03 (m, 2H), 2.97-2.82 (m, 2H), 2.27 (s, 3H), 2.17-2.05 (m, 2H), 1.85-1.60 (m, 3H); MS (ESI+) m/z 405 (M+H); HPLC>99% (AUC), tR=23.81 min.

Workup

  1. customThe reaction mixture was quenched with saturated solution of sodium bicarbonate
  2. concentrationconcentrated under reduced pressure
  3. customThe crude was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-a2acf632a5304e4c9143ace5c246ee31
Source dataset
uspto-grants-2007_12
Patent number
US07307094B2

Reaction notes

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