Benzaldehyde → HCID 90037087, compound

HRID 2205669Notes

Reaction equation

HRID 2205669 reaction equation
[NH2:1][C@H:2]([C:12]1[O:13][C:14]([C:17]2[C:18]([O:27][CH3:28])=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:39](C)=O.[Na+].C=O.O>ClC(Cl)C.C(Cl)Cl>[CH2:29]([N:1]([CH3:39])[C@H:2]([C:12]1[O:13][C:14]([C:17]2[C:18]([O:27][CH3:28])=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][N:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:11])[CH2:9][CH3:10])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydride2×HCID 90036926HCID 90036926, compound

Product 1

HCID 90037087HCID 90037087, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

(S)-9-amino-9-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)nonan-3-one (0.21 mmol, 1 eq), prepared as described above, was solubilized in dichloroethane (2.1 mL) and treated with benzaldehyde (0.17 mmol, 0.8 eq). The mixture was stirred 1 h at room temperature then treated with NaBH(AcO)3 (0.21 mmol, 1 eq). After stirring 30 min at room temperatures, a 37% solution of HCHO in water (3 eq) and NaBH(AcO)3 (0.21 mmol, 3 eq). After 10 minutes, the mixture was diluted with DCM and washed with water and brine. The organic phase was dried, filtered and concentrated. Residue was purified by flash chromatography using EtOAc/Petroleum Ether in a linear gradient from 4% to 40% of EtOAc. The product was obtained as a colorless oil in 53% yield. MS (ES) C30H35N3O3 requires: 485.62, found: 486. 1H-NMR (300 MHz, DMSO-d6) δ: 8.58 (1 H, s), 8.05 (1 H, d, J=5.4 Hz), 7.81 (1 H, d, J=6.3 Hz), 7.71 (2 H, m). 7.49 (1 H, t, J=5.4 Hz), 7.34-7.30 (4 H, m), 7.27-7.22 (1 H, m), 4.17 (3 H, s), 3.95 (1 H, t, J=5.7 Hz), 3.72 (1 H, d, J=10.2 Hz), 3.49 (1 H, d, J=10.2 Hz), 2.41-2.34 (2 H, m), 2.18 (3 H, s), 1.99-1.93 (2 H, m), 1.50-1.41 (4 H, m), 1.27-1.23 (4 H, m), 0.89 (3 H, t, J=5.4 Hz).

Workup

  1. stirringAfter stirring 30 min at room temperatures
  2. waitAfter 10 minutes
  3. washwashed with water and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customResidue was purified by flash chromatography
  8. customThe product was obtained as a colorless oil in 53% yield

Sources & evidence

ORD record
ord-7e11c377043245568feef32271f61dce
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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