Diethyl Ether → HCID 86662317, compound

HRID 337317Notes

Reaction equation

HRID 337317 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[CH:13][C:14]([O:17][C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:15][CH:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66741956HCID 66741956, compound

Product 1

HCID 86662317HCID 86662317, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-chloro-4-(5-(1-hydroxy-2-methylpropan-2-yloxy)pyridin-2-ylamino)-2-methylpyridazin-3(2H)-one (750 mg, 2.31 mmol, Eq: 1.00) in DCM (100 ml) was added Dess-Martin periodinane (1.27 g, 3.00 mmol, Eq: 1.30). The reaction mixture was stirred at room temperature for about 40 minutes. Ether was added (100 mL) followed by 50 ml NaOH solution (1 M). The mixture was stirred for additional 15 minutes and transferred to separatory funnel. The organic layer was washed with equal volume of NaOH (1M) water (50 mL), dried (Na2SO4) and evaporated under vacuum to afford the desired product (668 mg) as a light brown powder. (M+H)=323 m/e. 1H NMR (400 MHz, DMSO-d6) 8 ppm 1.36 (s, 6 H) 3.68 (s, 3 H) 7.43-7.47 (m, 1 H) 7.51-7.55 (m, 1 H) 8.10 (dd, J=3.03, 0.51 Hz, 1 H) 8.27 (s, 1 H) 9.69 (s, 1 H) 9.82 (s, 1 H).

Workup

  1. stirringThe mixture was stirred for additional 15 minutes
  2. customtransferred to separatory funnel
  3. washThe organic layer was washed with equal volume of NaOH (1M) water (50 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-d8a41e7afc18404fbac3a139a96e42a2
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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