Hydrochloric Acid → HCID 66751231, compound

HRID 2043343Notes

Reaction equation

HRID 2043343 reaction equation
CN(C)S([N:6]1[C:10]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([CH:20]3[O:24][CH2:23][CH2:22][O:21]3)[C:14]=2[F:25])=[CH:9][N:8]=[CH:7]1)(=O)=O.Cl.O1CCO[CH2:30][CH2:29]1>O1CCCC1>[O:24]1[CH2:23][CH2:22][O:21][CH:20]1[C:15]1[C:14]([F:25])=[C:13]([N:12]([CH2:29][CH3:30])[CH2:11][C:10]2[NH:6][CH:7]=[N:8][CH:9]=2)[CH:18]=[CH:17][C:16]=1[F:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66751678HCID 66751678, compound

Product 1

HCID 66751231HCID 66751231, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-[(3-[1,3]dioxolan-2-yl-2,4-difluoro-phenylamino)-methyl]-imidazole-1-sulfonic acid dimethylamide (0.53 g, 1.27 mmol) in tetrahydrofuran (10 ml) was added a 4 N solution of hydrogen chloride in dioxane (3.87 ml, 15.5 mmol) and the mixture was stirred at room temperature for 24 h. The mixture was then concentrated in vacuo and the residue taken up in dichloromethane/methanol (95:5) and washed with 1 N aq. sodium hydroxide solution. The layers were separated and the aqueous phase was back extracted twice with dichloromethane/methanol (95:5). The combined organic phases were washed with saturated brine, then dried over magensium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient) to yield a colourless gum (225 mg, 57%); MS (ISP): 310.3 ((M+H)+.).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with 1 N aq. sodium hydroxide solution
  3. customThe layers were separated
  4. extractionthe aqueous phase was back extracted twice with dichloromethane/methanol (95:5)
  5. washThe combined organic phases were washed with saturated brine
  6. dry with materialdried over magensium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-e96c3cfc8eda403b94e27ee34f2db17d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

Loading…