Hydrochloric Acid → HCID 53628423, compound

HRID 2388904Notes

Reaction equation

HRID 2388904 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[F:5][C:6]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([NH:16][S:17]([N:20]2[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]2)(=[O:19])=[O:18])[CH:13]=[C:12]([O:27][CH3:28])[N:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].Cl>C(Cl)Cl.C(O)(=O)C>[CH:1]1([NH:4][CH:23]2[CH2:24][CH2:25][N:20]([S:17]([NH:16][C:14]3[CH:13]=[C:12]([O:27][CH3:28])[N:11]=[C:10]([S:9][CH2:8][C:7]4[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:6]=4[F:5])[N:15]=3)(=[O:18])=[O:19])[CH2:21][CH2:22]2)[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 67051257HCID 67051257, compound

Product 1

HCID 53628423HCID 53628423, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclopropylamine (0.08 mL) in DCM (2 mL) was added to a solution of acetic acid (0.025 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 3M aqueous sodium hydroxide (6 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 water, saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated. The crude material 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: 21 mg

Workup

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

Sources & evidence

ORD record
ord-0fe1cf6c78c74fa6af6643861cb9089c
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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