Methyl iodide → HCID 68291095, compound

HRID 1507930Notes

Reaction equation

HRID 1507930 reaction equation
IC.[CH:3]1([C@H:6]([NH:8][C:9]2[C:10]3[N:11]([CH:18]=[C:19]([C:21]4[O:22][C:23](=[S:26])[NH:24][N:25]=4)[CH:20]=3)[N:12]=[CH:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH3:7])[CH2:5][CH2:4]1.[CH2:27](N(CC)CC)C>CCO>[CH:3]1([C@H:6]([NH:8][C:9]2[C:10]3[N:11]([CH:18]=[C:19]([C:21]4[O:22][C:23]([S:26][CH3:27])=[N:24][N:25]=4)[CH:20]=3)[N:12]=[CH:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH3:7])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 86706848HCID 86706848, compound

Product 1

HCID 68291095HCID 68291095, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Iodomethane (0.069 ml, 1.111 mmol) was added in one portion to a stirred solution of (R)-4-(1-cyclopropylethylamino)-6-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide (Example 126, 306 mg, 0.889 mmol) and triethylamine (0.310 ml, 2.221 mmol) in absolute EtOH (3.55 ml). The reaction mixture was allowed to stir at rt for 2 hrs before evaporating in vacuo. The residue was then partitioned between 1N HCl and ethyl acetate. The organic layer was dried (MgSO4) and evaporated in vacuo. The residue was treated with MeOH and the solid filtered to give the title compound (135 mg, 0.377 mmol, 42.4% yield) as a white solid. The filtrate (which contained the remainder of the product) was evaporated and retained. HPLC (condition B): retention time=3.98 min. LCMS (condition B): MH+ m/z 358.9. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.88 (1 H, d, J=8.32 Hz), 8.31 (1 H, s), 8.27 (1 H, d, J=1.66 Hz), 7.32 (1 H, d, J=1.94 Hz), 3.89-4.04 (1 H, m), 3.30 (3 H, s), 1.34 (3 H, d, J=6.38 Hz), 1.01-1.20 (1 H, m), 0.44-0.58 (2 H, m), 0.35-0.44 (1 H, m), 0.20-0.35 (1 H, m).

Workup

  1. custombefore evaporating in vacuo
  2. customThe residue was then partitioned between 1N HCl and ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated in vacuo
  5. additionThe residue was treated with MeOH
  6. filtrationthe solid filtered

Sources & evidence

ORD record
ord-b193a5ccb80f40b98e4fe5caf4a31a22
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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