Dichloromethane → HCID 86687724, compound

HRID 1473651Notes

Reaction equation

HRID 1473651 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21](CC4C=CC(OC)=CC=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[C:11](=[O:36])[NH:10][N:9]=2)[CH:7]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[C:11](=[O:36])[NH:10][N:9]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86687723HCID 86687723, compound

Product 1

HCID 86687724HCID 86687724, compoundYield 72.7%

Procedure

In a vial, 1-(5-chloro-2-methoxyphenyl)-N-(4-methoxybenzyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydrophthalazine-6-sulfonamide (56 mg, 0.098 mmol) was dissolved in DCM (984 μl, 0.098 mmol) and then TFA (37.9 μl, 0.492 mmol) was added. After 30 min at rt, LCMS showed product. The reaction was quenched with saturated aqueous NaHCO3 (1 mL). White solid precipitated out of the solution and was filtered off with the aid of water. The solid was washed with 3 mL of water and dried to afford 1-(5-chloro-2-methoxyphenyl)-4-oxo-N-(thiazol-2-yl)-3,4-dihydrophthalazine-6-sulfonamide (32 mg, 72.4% yield). m/z (ESI) 449.0 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (1 mL)
  2. customWhite solid precipitated out of the solution
  3. filtrationwas filtered off with the aid of water
  4. washThe solid was washed with 3 mL of water
  5. customdried

Sources & evidence

ORD record
ord-75a6f4440e924af9bf67b7c789aa81e4
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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