Benzaldehyde → Benzyl-[2-(1,4-diaza-bicyclo[3.2.2]non-4-YL)-benzooxazol-5-YL]-amine

HRID 1815768Notes

Reaction equation

HRID 1815768 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][C:22]([N:24]3[CH:30]4[CH2:31][CH2:32][N:27]([CH2:28][CH2:29]4)[CH2:26][CH2:25]3)=[N:21][C:20]=2[CH:33]=1.[CH:34](=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[OH-].[Na+]>ClCCCl>[CH2:34]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][C:22]([N:24]3[CH:30]4[CH2:29][CH2:28][N:27]([CH2:32][CH2:31]4)[CH2:26][CH2:25]3)=[N:21][C:20]=2[CH:33]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 155158954-(5-Amino-benzooxazol-2-YL)-1,4-diaza-bicyclo[3.2.2]nonane

Product 1

HCID 22495787Benzyl-[2-(1,4-diaza-bicyclo[3.2.2]non-4-YL)-benzooxazol-5-YL]-amineYield 53.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (118 mg, 0.56 mmol) was added to a solution of 4-(5-amino-benzooxazol-2-yl)-1,4-diaza-bicyclo[3.2.2]nonane (52 mg, 0.20 mmol, prepared as in Example 39) and benzaldehyde (21 μL, 0.204 mmol) in 1,2-dichloroethane. The resulting mixture was allowed to stir at RT for a period of 3 h. at which time 2 mL of 1 N NaOH solution was added. The aqueous layer was extracted with CDCl3 (3×) and the combined organic layers were washed with water and brine and then dried (Na2SO4), filtered and concentrated. The crude residue was purified by chromatography (Biotage, 25M) eluting with 6% MeOH in CDCl3 containing 1 mL of NH4OH per L of eluent to give 37 mg of the title compound as an oil: 1H NMR CDCl3, 400 MHz) δ 7.37-7.29 (m, 3H), 7.25-7.22 (m, 2H), 7.00 (d, 1H, J=8.7 Hz), 6.64 (d, 1H, J=2.1 Hz), 6.27 (dd, 1H, J=8.7, 2.1 Hz), 4.47-4.45 (m, 1H), 4.30 (s, 2H), 3.87 (t, 2H, J=5.8 Hz), 3.16-3.09 (m, 4H), 3.01-2.96 (m, 2H), 2.15-2.08 (m, 2H), 1.81-1.73 (m, 2H): 13C NMR (CDCl3, 100 MHz) δ 146.0, 145.1, 142.0, 139.8, 128.8, 127.7, 127.3, 108.8, 106.0, 100.6, 57.3, 50.1, 49.4, 46.5, 44.1, 27.0; MS (Cl) m/z 349.2 (M+1).

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with CDCl3 (3×)
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by chromatography (Biotage, 25M)
  8. washeluting with 6% MeOH in CDCl3 containing 1 mL of NH4OH per L of eluent

Sources & evidence

ORD record
ord-ea3005a22a7345d78c5b3463eda416fd
Source dataset
uspto-grants-2005_04
Patent number
US06881734B2

Reaction notes

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