Triethylamine → HCID 23117129, compound

HRID 1921261Notes

Reaction equation

HRID 1921261 reaction equation
C(OC([O:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=O)(C)(C)C.[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH3:27])=[N:23][NH:24]2)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(#N)C.CN(C1C=CN=CC=1)C>[C:12]([O:11][C:9]([O:8][N:24]1[C:25]2[C:21](=[CH:20][CH:19]=[C:18]([O:17][CH3:16])[CH:26]=2)[C:22]([CH3:27])=[N:23]1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 178487565HCID 178487565, compound

Product 1

HCID 23117129HCID 23117129, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

Di-tert-butyl-dicarbonate in acetonitrile was mixed at 0° C. with 6-methoxy-3-methyl-1H-indazole (prepared following the procedure described by F. Dennler, Tetrahedron, 22, 1966, 3131-3139) (26.27 g, 0.162 mol), acetonitrile (200 ml), triethylamine (25 ml, 0.178 mol), DMAP (3.96 g, 0.0324 mol). The mixture was stirred at room temperature overnight. Acetonitrile was concentrated under vacuum. The mixture was extracted with ethylacetate and acidified at pH=2 with a solution of concentrated HCl, dried over Na2SO4, filtered and put in diisopropylether. 23.9 g of the expected product were obtained (as solid, 59%).

Workup

  1. customprepared
  2. concentrationAcetonitrile was concentrated under vacuum
  3. extractionThe mixture was extracted with ethylacetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-19daab997e394a40a178406cf7242576
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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