Chloromethyl Methyl Ether → HCID 117653471, compound

HRID 2178119Notes

Reaction equation

HRID 2178119 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[N:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].CCN(C(C)C)C(C)C.Cl[CH2:30][O:31][CH3:32]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:30][O:31][CH3:32])[C:14]2[N:15]=[N:16][CH:17]=[CH:18][CH:19]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 116787092HCID 116787092, compound

Product 1

HCID 117653471HCID 117653471, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-4-fluoro-N-(pyridazin-3-yl)benzenesulfonamide (Preparation 6, 6.70 g, 24.1 mmol) in DCM (150 mL) at 0° C. was added DIPEA (6.48 mL, 35.18 mmol) followed by chloromethoxymethane (1.46 mL, 25.54 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched by the addition of 1N NaOH (aq) solution, the organic layer was collected, washed with water, brine, and dried over Na2SO4 before concentrating in vacuo. The residue was purified using silica gel column chromatography eluting with EtOAc:Heptane 1:1 to afford the title compound as a mixture of isomers (3.85 g, 49%) that was used without further purification.

Workup

  1. customThe reaction mixture was quenched by the addition of 1N NaOH (aq) solution
  2. customthe organic layer was collected
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationbefore concentrating in vacuo
  6. customThe residue was purified
  7. washeluting with EtOAc:Heptane 1:1

Sources & evidence

ORD record
ord-87b8218afe1344a3ab48f9a5c1195bd8
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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