Triethylamine → HCID 67336209, compound

HRID 1672161Notes

Reaction equation

HRID 1672161 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Br[C:12]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(O)C.C(Cl)Cl>[CH2:19]([O:18][C:16]([C:12]1([NH:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:15][CH2:14][CH2:13]1)=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 880121H-Indazol-5-amineHCID 97595Ethyl 1-bromocyclobutanecarboxylate

Product 1

HCID 67336209HCID 67336209, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1H-indazol-5-ylamine (5.0 g, 37.6 mmol), ethyl 1-bromocyclobutane carboxylate (7.78 g, 6.08 mL, 37.6 mmol) and triethylamine (7.60 g, 10.5 mL, 75.1 mmol) in ethanol (5 mL) was heated at 100° C. for 3 days, then at 140° C. for 2 days. The reaction mixture was cooled to ambient temperature, and after 7 days the mixture was diluted with DCM (50 mL) and filtered. The filtrate was concentrated in vacuo then purified by chromatography (silica, 2 to 10% of a 9:1 MeOH:NH4OH solution in DCM) to give 1-(1H-indazol-5-ylamino)-cyclobutanecarboxylic acid ethyl ester (1.68 g, 6.49 mmol, 17%) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthen purified by chromatography (silica, 2 to 10% of a 9:1 MeOH:NH4OH solution in DCM)

Sources & evidence

ORD record
ord-dc4aaaf3f78943f8886051a335932779
Source dataset
uspto-grants-2011_08
Patent number
US07998963B2

Reaction notes

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