Sodium periodate → Tert-butyl (1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 339677Notes

Reaction equation

HRID 339677 reaction equation
I([O-])(=O)(=O)=O.[Na+].[C:7]([O:11][C:12](=[O:44])[NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([C:31]2[N:35]4[CH:36]=[CH:37][C:38]([CH:40]([OH:43])CO)=[CH:39][C:34]4=[N:33][N:32]=2)[CH:27]=[CH:26]3)[CH2:17][CH2:16]1)([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl>[C:7]([O:11][C:12](=[O:44])[NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]=2[N:29]=[C:28]([C:31]2[N:35]4[CH:36]=[CH:37][C:38]([CH:40]=[O:43])=[CH:39][C:34]4=[N:33][N:32]=2)[CH:27]=[CH:26]3)[CH2:17][CH2:16]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 86654349Tert-butyl (1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86654350Tert-butyl (1-(2-(7-formyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of silica gel (0.1 g) in DCM (3 mL) was added sodium periodate (0.13 mL, 0.087 mmol). The reaction was stirred for 10 minutes. tert-Butyl(1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (30 mg, 0.058 mmol) in DCM (2 mL) was then added to the slurry. The reaction was stirred for 30 minutes, then filtered and washed with DCM (20 mL). The organic layer was concentrated to give crude product.

Workup

  1. stirringThe reaction was stirred for 30 minutes
  2. filtrationfiltered
  3. washwashed with DCM (20 mL)
  4. concentrationThe organic layer was concentrated
  5. customto give crude product

Sources & evidence

ORD record
ord-a25b4140a6b9414a91fcee4474ba221c
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

Loading…