Sodium periodate → HCID 66858606, compound

HRID 1803316Notes

Reaction equation

HRID 1803316 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Cl:7][C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:37]=[C:23]4[C@@H:24]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=5)[CH2:25][C:26](=C)[CH2:27][CH2:28][N:22]4[N:21]=3)=[CH:15][C:14]=2[O:38][CH3:39])[CH:12]=1>O.C1COCC1.[Cl-].[Na+].O.[Os](=O)(=O)(=O)=O>[Cl:7][C:8]1[N:9]=[CH:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[N:37]=[C:23]4[C@@H:24]([C:30]5[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=5)[CH2:25][C:26](=[O:2])[CH2:27][CH2:28][N:22]4[N:21]=3)=[CH:15][C:14]=2[O:38][CH3:39])[CH:12]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 58110092HCID 58110092, compound

Product 1

HCID 66858606HCID 66858606, compoundYield 95.6%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of sodium periodate (276 mg, 1.29 mmol) in water (5.0 mL) was added over a 10 min period to a vigorously stirred solution of the (R)—N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-9-(4-fluorophenyl)-7-methylene-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (200 mg, 0.430 mmol, from example 134) and osmium tetroxide (10.9 mg, 0.043 mmol) in THF (5.0 mL). The reaction was stirred for 1 h and then diluted with water (150 mL)/brine (100 mL) and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford (R)-2-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-9-(4-fluorophenyl)-8,9-dihydro-5H-[1,2,4]triazolo[1,5-a]azepin-7(6H)-one (192 mg, 77% yield). LC-MS (M+H)+ 467.1.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92b6f4b42add487daeeff3aca8899e8d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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