Sulfuric Acid → HCID 59437262, compound

HRID 244478Notes

Reaction equation

HRID 244478 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH3:38])[C:6]([C:8]1[N:9]([CH2:35][CH:36]=[CH2:37])[CH:10]=[C:11]([C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[N:23]=[CH:22]3)([OH:18])[C:14]([F:17])([F:16])[F:15])[CH:12]=1)=[O:7].OS(O)(=O)=O>CCOCC>[CH2:35]([N:9]1[C:8]2[C:6](=[O:7])[N:5]([CH3:38])[CH:4]=[CH:3][C:12]=2[C:11]([C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[N:23]=[CH:22]3)([OH:18])[C:14]([F:15])([F:16])[F:17])=[CH:10]1)[CH:36]=[CH2:37]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59437227HCID 59437227, compound

Product 1

HCID 59437262HCID 59437262, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A room temperature solution of 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid (2,2-dimethoxyethyl)methylamide (100 mg, 0.178 mmol) in ether (2 mL) was added H2SO4 (50 μL). After 13 hours, the mixture was carefully quenched with saturated aqueous sodium bicarbonate (3 mL) and extracted with three 10 mL portions of ethyl acetate. The combined organic layers were washed with brine (10 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by chromatography on SiO2 (0-80% ethyl acetate in hexanes, gradient) to give 84 mg (95%) of the title compound. MS m/z 497.36 (MH+), m.p. 91° C.-93° C.

Workup

  1. customthe mixture was carefully quenched with saturated aqueous sodium bicarbonate (3 mL)
  2. extractionextracted with three 10 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on SiO2 (0-80% ethyl acetate in hexanes, gradient)

Sources & evidence

ORD record
ord-593278c787e9496c8e53b47cd2814131
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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