Hydrochloric Acid → HCID 53628422, compound

HRID 2388897Notes

Reaction equation

HRID 2388897 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][C:17]=1[CH2:18][S:19][C:20]1[N:25]=[C:24]([NH:26][S:27]([N:30]2[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]2)(=[O:29])=[O:28])[CH:23]=[C:22]([O:37][CH3:38])[N:21]=1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[F:15][C:16]1[C:42]([F:43])=[CH:41][CH:40]=[CH:39][C:17]=1[CH2:18][S:19][C:20]1[N:25]=[C:24]([NH:26][S:27]([N:30]2[CH2:31][CH2:32][CH:33]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH2:34][CH2:35]2)(=[O:29])=[O:28])[CH:23]=[C:22]([O:37][CH3:38])[N:21]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 67051257HCID 67051257, compound

Product 1

HCID 53628422HCID 53628422, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.48 g) was added to a solution of N-(2-[(2,3-difluorobenzyl)thio]-6-methoxypyrimidin-4-yl}-4-oxopiperidine-1-sulfonamide (the product of step iii) (0.249 g), morpholine (0.2 mL) and 2 M aqueous acetic acid (0.5 mL) in DCM (12 mL). The mixture was stirred at room temperature for 18 h then 2 M aqueous sodium hydroxide (10 mL) added to the residue. The mixture was shaken vigorously then acidified to pH 8 with 2 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica using a 3:7 to 1:0 mixture of ethyl acetate and iso-hexane as eluent then precipitated slowly from methanol, filtered and washed with further methanol to afford the title compound as a pale yellow solid. Yield: 53 mg

Workup

  1. stirringThe mixture was shaken vigorously
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica using a 3:7
  8. additionto 1:0 mixture of ethyl acetate and iso-hexane as eluent
  9. customthen precipitated slowly from methanol
  10. filtrationfiltered
  11. washwashed with further methanol

Sources & evidence

ORD record
ord-2a0669cb8ec8436b99e57cc501d39eb3
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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