Ethyl Acetate → HCID 68232205, compound

HRID 869186Notes

Reaction equation

HRID 869186 reaction equation
O.O.[Sn](Cl)Cl.[N:6]([CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[N:19][C:18]([N:21]([CH2:29][C:30]3([C:34]4[C:39]([F:40])=[CH:38][CH:37]=[CH:36][N:35]=4)[CH2:33][CH2:32][CH2:31]3)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:16]=2)=[N:12][CH:11]=1)=[N+]=[N-].C(OCC)(=O)C>CO>[NH2:6][CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[N:19][C:18]([N:21]([CH2:29][C:30]3([C:34]4[C:39]([F:40])=[CH:38][CH:37]=[CH:36][N:35]=4)[CH2:33][CH2:32][CH2:31]3)[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[CH:17][CH:16]=2)=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 86686137HCID 86686137, compound

Product 1

HCID 68232205HCID 68232205, compoundYield 185.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tin(II) chloride dihydrate (15.5 g, 80 mmol) was added to a solution of t-butyl 6-(5-(azidomethyl)thiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (20 g, 40 mmol) in methanol (400 mL) and the reaction was stirred at rt for 30 min. The reaction was poured into ethyl acetate (1000 mL), washed with water (3×200 mL), and the combined organic layers were separated, dried over Na2SO4, filtered, concentrated, and purified using silica gel column chromatography (9% MeOH/90% EtOAc/1% TEA) to give 35 g of t-butyl 6-(5-(aminomethyl)thiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate as a yellow oil.

Workup

  1. washwashed with water (3×200 mL)
  2. customthe combined organic layers were separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-8390e72a56d24c8180abdb3f6f5af93f
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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