Hydrochloric Acid → HCID 70937947, compound

HRID 532526Notes

Reaction equation

HRID 532526 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[CH:16]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[S:15][CH2:14][C@H:13]([N:25]2[CH2:32][C:31]3[C:27](=[N:28][N:29]([CH2:33][C:34](OC)=[O:35])[CH:30]=3)[CH2:26]2)[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>CO>[F:24][C:18]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=1[CH:16]1[C@@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[CH2:12][C@@H:13]([N:25]2[CH2:32][C:31]3[C:27](=[N:28][N:29]([CH2:33][CH2:34][OH:35])[CH:30]=3)[CH2:26]2)[CH2:14][S:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 70926726HCID 70926726, compound

Product 1

HCID 70937947HCID 70937947, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (26.4 mg, 0.698 mmol) was added in 3 portions over 4 h to a solution of methyl 2-[5-[(3R,5S)-5-(tert-butoxycarbonylamino)-6-(2,5-difluorophenyl)tetrahydrothiopyran-3-yl]-4,6-dihydropyrrolo[3,4-c]pyrazol-2-yl]acetate (13.2 mg, 0.025 mmol) in methanol (0.25 mL). After an additional 15 min, 2N HCl (0.1 mL, 0.1 mmol) was added and the resulting suspension was stirred at room temperature for 5 min. Filtration of the suspension and purification by reverse-phase HPLC was followed by preparative thin layer plate chromatography (1×500 micron PTLC plate), developed with a 90:10 mixture of methylene chloride/(10:1 EtOH/concentrated ammonium hydroxide). The appropriate uv active band was removed, eluted with a 90:10 mixture of methylene chloride/(10:1 EtOH/concentrated ammonium hydroxide) and evaporated to give the title compound as a white solid. MS: 499.2 [M+1]

Workup

  1. filtrationFiltration of the suspension and purification by reverse-phase HPLC
  2. additiondeveloped with a 90:10 mixture of methylene chloride/(10:1 EtOH/concentrated ammonium hydroxide)
  3. customThe appropriate uv active band was removed
  4. washeluted with a 90:10 mixture of methylene chloride/(10:1 EtOH/concentrated ammonium hydroxide)
  5. customevaporated

Sources & evidence

ORD record
ord-d58c43e3cc0142649b204b87f12e77ed
Source dataset
uspto-grants-2014_10
Patent number
US08853212B2

Reaction notes

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