Triethylamine → HCID 67238715, compound

HRID 1748297Notes

Reaction equation

HRID 1748297 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C:10]1([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=3)[CH:16]=[C:15]2[C:28]([O:30]CC)=O)[CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[O:30]=[C:28]1[C:15]2=[CH:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:22]=3[N:14]2[CH2:13][C:10]2([CH2:12][CH2:11]2)[CH2:9][NH:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 67235374HCID 67235374, compound

Product 1

HCID 67238715HCID 67238715, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (36.3 mL, 260.8 mmol) is added to the mixture of crude diethyl 1-{[1-(aminomethyl)cyclopropyl]methyl}-1H-indole-2,6-dicarboxylate (30 g, 86.9 mmol) and K2CO3 (36 g, 260.8 mmol) in ethanol (800 mL). The reaction mixture is heated at 80° C. for 2 h and it is cooled to room temperature and stirred for another 16 h. 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 (9.2 g, 31% for 3 steps) as a white solid.

Workup

  1. temperatureit is cooled to room temperature
  2. customSolid 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-a19d2f56903148debd1673296f503bb6
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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