Triethylamine → HCID 23003068, compound

HRID 396135Notes

Reaction equation

HRID 396135 reaction equation
[C:1]([O:8]C([O-])=O)(=O)[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[CH3:12][C:13]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[C:30]([CH3:37])[C:14]=1[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][N:20]=[C:19]2[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(N(CC)CC)C.C(OCC)(=O)C>CN(C)C1C=CN=CC=1.O1CCCC1.C(#N)C>[C:3]([O:2][C:1]([N:21]1[C:22]2[C:18](=[CH:17][C:16]([O:15][C:14]3[C:30]([CH3:37])=[CH:31][C:32]([N+:34]([O-:36])=[O:35])=[CH:33][C:13]=3[CH3:12])=[CH:24][CH:23]=2)[C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[N:20]1)=[O:8])([CH3:4])([CH3:5])[CH3:6]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22064466Tert-butyldicarbonateHCID 178442320HCID 178442320, compound

Product 1

HCID 23003068HCID 23003068, compoundYield 102%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

889 mg (4.074 mmol) of tert-butyl pyrocarbonate are added at 0° C. to a suspension of 1.20 g (3.395 mmol) of 5(2,6-dimethyl-4-nitrophenoxy)-3-pentyl-1H-indazole (Example XX), 378 mg (3.735 mmol) of triethylamine and 41 mg (0.340 mmol) of 4-dimethylaminopyridine in 5 ml of tetrahydrofuran and 5 ml of acetonitrile and the mixture is stirred at room temperature for 30 min. The reaction mixture is then freed from the solvent in vacuo, taken up with ethyl acetate, and the organic phase is washed once each with 1N hydrochloric acid, satd sodium hydrogencarbonate solution and satd. sodium chloride solution, dried over sodium sulphate, freed from the solvent in vacuo and purified on silica gel using methylene chloride. 1.57 g (92% of theory) of 1-tert-butoxycarbonyl-5-(2,6-dimethyl-4-nitrophenoxy)-3-pentyl-1H-indazole are obtained.

Workup

  1. washthe organic phase is washed once each with 1N hydrochloric acid, satd sodium hydrogencarbonate solution
  2. dry with materialsodium chloride solution, dried over sodium sulphate
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-d613fb76d79f4b7c89e1118a3e167915
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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