Hydrochloric Acid → HCID 178425817, compound

HRID 1988937Notes

Reaction equation

HRID 1988937 reaction equation
[CH:1]1([NH:4][C:5](=[O:40])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:21]=[C:20]4[C:16]([C:17]([S:30]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)(=[O:32])=[O:31])=[N:18][N:19]4COCC[Si](C)(C)C)=[CH:15][CH:14]=3)[CH:7]=2)[CH2:3][CH2:2]1.Cl>CO>[CH:1]1([NH:4][C:5](=[O:40])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:21]=[C:20]4[C:16]([C:17]([S:30]([C:33]5[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=5)(=[O:32])=[O:31])=[N:18][NH:19]4)=[CH:15][CH:14]=3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58656465HCID 58656465, compound2×

Product 1

HCID 178425817HCID 178425817, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-cyclopropyl-3-[3-[(4-fluorophenyl)sulfonyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazol-6-yl]-4-methylbenzamide (Intermediate 71) (0.05 g) in methanol (1.5 ml) was added conc hydrochloric acid (0.75 ml). The solution was heated at reflux for 15 h then left at room temp. for 18 h. The solution was concentrated under vacuum then purified on a Varian Bond-Elut SPE cartridge (silica, 5 g) eluting with cyclohexane:ethyl acetate (1:1) to give the title compound (0.01 g).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 15 h
  3. concentrationThe solution was concentrated under vacuum
  4. customthen purified on a Varian Bond-Elut SPE cartridge (silica, 5 g)
  5. washeluting with cyclohexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5c6097ea463c4e0aa978a59e3074376a
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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