Triethylamine → HCID 21183710, compound

HRID 1385096Notes

Reaction equation

HRID 1385096 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15](Cl)=[O:16])[CH:13]=3)[C:8]([CH2:18][CH3:19])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([NH:35][C:15]([C:12]2[CH:13]=[C:14]3[C:9]([C:8]([CH2:18][CH3:19])=[N:7][N:6]3[CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:10][CH:11]=2)=[O:16])[CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 15545850HCID 15545850, compound

Product 1

HCID 21183710HCID 21183710, compoundYield 104.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

87 mg (0.708 mmol, 1.0 equiv) DMAP were added to a room temperature solution of 196 mg (0.708 mmol, 1.0 equiv) 1-cyclopentyl-3-ethyl-1H-indazole-6-carbonyl chloride, 99μL (0.708 mmol, 1.0 equiv) triethylamine and 80 μL (0.708 mmol, 1.0 equiv) m-anisidine in 5 mL CH2Cl2. After 48 hours, the reaction mixture was diluted with 75 mL ethyl acetate, washed 2×15 mL 1N HCl, 1×15 mL H2O, 1×15 mL brine, and dried over MgSO4. Filtration, concentration of filtrate and drying gave 0.27 g of an amber solid, which was purified by silica gel chromatography (ethyl acetate/hexanes gradient 10% (20%) to give 118 mg of a clear oil. Crystallization from petroleum ether gave 75 mg (29%) of a white powder: mp 91-93° C.; Anal. calcd for C22H25N3O2: C, 72.71; H, 6.95; N, 11.56. Found: C, 72.35; H, 7.15; N, 11.47.

Workup

  1. washwashed 2×15 mL 1N HCl, 1×15 mL H2O, 1×15 mL brine
  2. dry with materialdried over MgSO4
  3. filtrationFiltration, concentration of filtrate
  4. customdrying

Sources & evidence

ORD record
ord-0fded2a121b54423b18bed940b2e05fb
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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