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 1041965Notes

Reaction equation

HRID 1041965 reaction equation
I([O-])(=O)(=O)=O.[Na+].[OH:7][CH:8]([C:11]1[CH:16]=[CH:15][N:14]2[C:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[C:23]([N:30]5[CH2:35][CH2:34][CH:33]([CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:32][CH2:31]5)[CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[N:18][N:19]=[C:13]2[CH:12]=1)CO>C(Cl)Cl>[CH:8]([C:11]1[CH:16]=[CH:15][N:14]2[C:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[C:23]([N:30]5[CH2:31][CH2:32][CH:33]([CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[CH2:34][CH2:35]5)[CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[N:18][N:19]=[C:13]2[CH:12]=1)=[O:7]

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-f56aba911ee54afe88a3757b2b4dc2dd
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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