Triethylamine → HCID 23117129, compound

HRID 1011478Notes

Reaction equation

HRID 1011478 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-f5cf9ca580ac46d0912094b586777bfb
Source dataset
uspto-grants-2011_07
Patent number
US07977364B2

Reaction notes

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