Acetic Acid → HCID 59558841, compound

HRID 1175536Notes

Reaction equation

HRID 1175536 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-deea9cd4d93f41e992dba016098d10e1
Source dataset
uspto-grants-2010_11
Patent number
US07838675B2

Reaction notes

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