Water → HCID 86671470, compound

HRID 1530591Notes

Reaction equation

HRID 1530591 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[C:19]([CH:22]=C)[N:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:24]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[O:25]1CCCC1.O.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O>[CH:1]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[C:19]([CH:22]=[O:25])[N:20]=[CH:21][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:24]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 68313172HCID 68313172, compound

Product 1

HCID 86671470HCID 86671470, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-10-vinyl-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine (0.500 g, 0.00155 mol) was dissolved in Tetrahydrofuran (30 mL, 0.4 mol) and Water (20 mL, 1 mol). Osmium tetraoxide 4% (wt) in water (0.758 mL, 0.000124 mol) was added. Followed by sodium metaperiodate (0.664 g, 0.00310 mol). The reaction mixture was stirred overnight at room temperature. LC-MS analysis of the reaction mixture showed complete conversion to desired product [C]. The crude reaction mixture was quenched with saturated sodium thiosulfate, diluted with EtOAc, and extracted 3×. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to dryness to give 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine-10-carbaldehyde.

Sources & evidence

ORD record
ord-86ef484cabda47dc88ed8df88bfef801
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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