Hydrochloric Acid → HCID 59455975, compound

HRID 1874747Notes

Reaction equation

HRID 1874747 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([NH:27][S:28]([C:31]1[S:32][C:33]([Cl:36])=[CH:34][CH:35]=1)(=[O:30])=[O:29])=[N:9][N:10]2[CH2:15][C:16]1[CH:17]=[C:18]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:19]=[CH:20][CH:21]=1)(=[O:5])[CH3:4].Cl>CO>[Cl:36][C:33]1[S:32][C:31]([S:28]([NH:27][C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[CH:14][C:6]=3[CH:3]([OH:5])[CH3:4])[N:10]([CH2:15][C:16]3[CH:17]=[C:18]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[CH:19]=[CH:20][CH:21]=3)[N:9]=2)(=[O:29])=[O:30])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59456023HCID 59456023, compound

Product 1

HCID 59455975HCID 59455975, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (3.09 mg, 0.082 mmol) was added to a stirring solution of N-({3-[(4-acetyl-3-{[(5-chloro-2-thienyl)sulfonyl]amino}-1H-indazol-1-yl)methyl]phenyl}methyl)acetamide (for a preparation see Intermediate 75) (40 mg, 0.068 mmol) in MeOH (2 mL) at 25° C. under nitrogen. The reaction mixture was stirred at room temp. for 2 hours, and then 1N HCl (5 mL) was slowly added and the methanol was evaporated in vacuo. The product was extracted with EtOAc (2×20 mL) and the combined organic layers were dried by passing through a hydrophobic frit and concentrated. The residue was dissolved in DMSO (1 mL) and purified by Mass Directed AutoPrep on Sunfire C18 column using Acetonitrile Water with a Formic acid modifier (Method A). The solvent was evaporated in vacuo to give the title compound (18 mg, 48%). LCMS (System A) RT=0.97 min, ES+ve m/z 519/521 (M+H)+.

Workup

  1. customat 25° C.
  2. customthe methanol was evaporated in vacuo
  3. extractionThe product was extracted with EtOAc (2×20 mL)
  4. customthe combined organic layers were dried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DMSO (1 mL)
  7. custompurified by Mass Directed AutoPrep on Sunfire C18 column
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-170ae8af40224b049a97233c2e5f2c7f
Source dataset
uspto-grants-2012_11
Patent number
US08304446B2

Reaction notes

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