Hydrochloric Acid → 3-[(1S)-2-Hydroxy-1-methylethoxy]-5-[(1-methyl-1H-indol-5-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548656Notes

Reaction equation

HRID 548656 reaction equation
Cl.[Si]([O:9][CH2:10][C@H:11]([CH3:39])[O:12][C:13]1[CH:14]=[C:15]([CH:25]=[C:26]([O:28][C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[CH:33]=[CH:32]3)[CH:27]=1)[C:16]([NH:18][C:19]1[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=1)=[O:17])(C(C)(C)C)(C)C.C(=O)(O)[O-].[Na+]>CO>[OH:9][CH2:10][C@H:11]([CH3:39])[O:12][C:13]1[CH:14]=[C:15]([CH:25]=[C:26]([O:28][C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[N:34]([CH3:38])[CH:33]=[CH:32]3)[CH:27]=1)[C:16]([NH:18][C:19]1[CH:23]=[CH:22][N:21]([CH3:24])[N:20]=1)=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 576631753-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(1-methyl-1H-indol-5-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 159492133-[(1S)-2-Hydroxy-1-methylethoxy]-5-[(1-methyl-1H-indol-5-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% Hydrochloric acid (0.5 mL) was added to a solution of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-[(1-methyl-1H-indol-5-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (120 mg, 0.22 mmol) in methanol (5 mL). The reaction was stirred at ambient temperature for 1 hour, saturated sodium bicarbonate solution added and the methanol evaporated. The aqueous residue was taken to pH 2 and extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with 1% methanol in ethyl acetate, to give the desired product (85 mg).

Workup

  1. customthe methanol evaporated
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas chromatographed on silica
  9. washeluting with 1% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f3dc03222feb42739324f90bcc8307d2
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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