Acetic Acid → HCID 59558841, compound

HRID 1959086Notes

Reaction equation

HRID 1959086 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(O)(=O)C.[F:12][C:13]1[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:14]=1[CH2:15][S:16][C:17]1[N:22]=[C:21]([NH:23][S:24]([N:27]2[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]2)(=[O:26])=[O:25])[CH:20]=[C:19]([O:34][CH3:35])[N:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:12][C:13]1[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:14]=1[CH2:15][S:16][C:17]1[N:22]=[C:21]([NH:23][S:24]([N:27]2[CH2:28][CH2:29][CH:30]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH2:31][CH2:32]2)(=[O:25])=[O:26])[CH:20]=[C:19]([O:34][CH3:35])[N:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 67051257HCID 67051257, compound

Product 1

HCID 59558841HCID 59558841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-methyl-piperazine (0.13 mL) in DCM (2 mL) was added to a solution of acetic acid (0.03 mL) and N-{2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-oxopiperidine-1-sulfonamide (the product of example 148, step iii) (0.10 g) in DCM (2 mL). The solution was stirred at room temperature for 1 h then sodium triacetoxyborohydride (0.24 g) was added in portions. The mixture was stirred at room temperature overnight then the DCM was evaporated and 3M aqueous sodium hydroxide (6 mL) added to the residue. The mixture was shaken vigorously then acidified to pH 8 with 2M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with water, saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated. The residue was purified by reverse phase HPLC (gradient 25-95% acetonitrile in 0.1% aqueous ammonium acetate) to afford the title compound as a white powder. Yield: 22 mg

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customthe DCM was evaporated
  3. addition3M aqueous sodium hydroxide (6 mL) added to the residue
  4. stirringThe mixture was shaken vigorously
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by reverse phase HPLC (gradient 25-95% acetonitrile in 0.1% aqueous ammonium acetate)

Sources & evidence

ORD record
ord-0c80abfa48e54a268ebb0a8aeaef916d
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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