1,2-Dichloroethane → HCID 67451027, compound

HRID 869184Notes

Reaction equation

HRID 869184 reaction equation
C(C[C:4]1[S:8][C:7]([C:9]2[N:14]=[N:13][C:12]([N:15]([CH2:23][C:24]3([C:28]4[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:27][CH2:26][CH2:25]3)C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[N:6][CH:5]=1)#N.Cl.CN.C1C=CC2N(O)N=[N:44][C:42]=2C=1.C(Cl)CCl.[C:52]([O:55]CC)(=O)[CH3:53]>Cl.CN(C=O)C>[F:34][C:33]1[C:28]([C:24]2([CH2:23][NH:15][C:12]3[N:13]=[N:14][C:9]([C:7]4[S:8][C:4]([CH2:53][C:52]([NH:44][CH3:42])=[O:55])=[CH:5][N:6]=4)=[CH:10][CH:11]=3)[CH2:25][CH2:26][CH2:27]2)=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 68231864HCID 68231864, compound

Product 1

HCID 67451027HCID 67451027, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of t-butyl 6-(5-(cyanomethyl)thiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (1 g, 2 mmol) in HCl (30 mL, conc) was heated to 105° C. in a microwave reactor and stirred for 15 min. The reaction was concentrated to give 900 mg (2.3 mmol) of a crude reddish solid. To this solid was added methylamine hydrochloride (183 mg, 2.7 mmol), HOBt (365 mg, 2.7 mmol), EDC (516 mg, 2.7 mmol), DMF (30 mL), and TEA (1.3 mL, 9 mmol). The reaction was stirred at rt overnight. The reaction was then poured into ethyl acetate (200 mL), washed with water (3×100 mL), and the organic layer was separated, dried over Na2SO4, filtered, concentrated, and recrystallized from EtOAc to give 408 mg of 2-(2-(6-((1-(3-Fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)thiazol-5-yl)-N-methylacetamide as a white solid (M+H=413.3).

Workup

  1. concentrationThe reaction was concentrated
  2. customto give 900 mg (2.3 mmol) of a crude reddish solid
  3. stirringThe reaction was stirred at rt overnight
  4. washwashed with water (3×100 mL)
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-b7690d34ee8a46aa8723bfc402a457ae
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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