HCID 69234263, compound → HCID 59843068, compound

HRID 1878749Notes

Reaction equation

HRID 1878749 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]2[S:20][CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:13]1)C(=O)OC(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:1][NH:2][CH2:10][CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[CH:15][C:14]([C:19]2[S:20][CH:21]=[C:22]([CH3:24])[CH:23]=2)=[N:13]1

Participants

4

Reactant 1

HCID 69234263HCID 69234263, compound

Product 1

HCID 59843068HCID 59843068, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl methyl(2-(3-(4-methylthiophen-2-yl)-6-oxopyridazin-1(6H)-yl)ethyl)carbamate (340 mg, 973 μmol) in CH2Cl2 (5 mL) and TFA (5 mL) was stirred for 30 min at 23° C. The solvents were removed under reduced pressure and the residue partitioned between CH2Cl2 (20 mL) and 1M NaOH (10 mL). The organic layer was dried over MgSO4, concentrated and purified on silica (12 g) eluting with 0-6% (2M NH3 in MeOH/CH2Cl2) to give the product as an amber oil. MS (ESI pos. ion) m/z (MH+): 250. Calc'd exact mass for C12H15N3OS: 249. 1H NMR (400 MHz, Chloroform-d) δ ppm 1.60 (br. s., 2 H) 2.28 (d, J=0.78 Hz, 3 H) 2.49 (s, 3 H) 3.07 (t, J=6.06 Hz, 2 H) 4.32 (t, J=6.06 Hz, 2 H) 6.88-7.01 (m, 2 H) 7.18 (d, J=1.17 Hz, 1 H) 7.54 (d, J=9.59 Hz, 1 H).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue partitioned between CH2Cl2 (20 mL) and 1M NaOH (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified on silica (12 g)
  6. washeluting with 0-6% (2M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-239019e5f79c42b48eeca6f24532360c
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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