Triethylamine → HCID 67237019, compound

HRID 1748300Notes

Reaction equation

HRID 1748300 reaction equation
C(N(CC)CC)C.C([O:10][C:11]([C:13]1[N:14]([CH2:27][C:28]2([CH2:32][NH2:33])[CH2:31][CH2:30][CH2:29]2)[C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:16]=2)=O)C.C([O-])([O-])=O.[K+].[K+]>C(O)C>[O:10]=[C:11]1[C:13]2=[CH:21][C:20]3[CH:19]=[CH:18][C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]=3[N:14]2[CH2:27][C:28]2([CH2:29][CH2:30][CH2:31]2)[CH2:32][NH:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67235939HCID 67235939, compound

Product 1

HCID 67237019HCID 67237019, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (23.3 mL, 167.5 mmol) is added to a mixture of crude 1-(1-aminomethyl-cyclobutylmethyl)-1H-indole-2,6-dicarboxylic acid diethyl ester from the preceding step and K2CO3 (23.16 g, 167.5 mmol) in ethanol (1.2 L). The reaction mixture is heated at 80° C. for 2 h then is cooled down to room temperature and stirred for another 16 h. The solid K2CO3 is removed by filtration and the filtrate is concentrated to afford the crude compound which is purified by flash column chromatography using 3% methanol in CH2Cl2 to afford the title compound (7 g, 40% for 3 steps) as a white solid.

Workup

  1. temperaturethen is cooled down to room temperature
  2. customThe solid K2CO3 is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customto afford the crude compound which
  5. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-fee12c41911b40c0a01cd147c42466bd
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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