Triethylamine → HCID 131735403, compound

HRID 630546Notes

Reaction equation

HRID 630546 reaction equation
ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C.[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([OH:29])=O)[CH:25]=2)[CH:20]=[CH:19]1.[NH:30]1[CH2:34][CH2:33][C@@H:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:31]1>CN(C=O)C.O>[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([N:30]3[CH2:34][CH2:33][C@@H:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH2:31]3)=[O:29])[CH:25]=2)[CH:20]=[CH:19]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 181649HOAtHCID 5952301H-indole-6-carboxylic acidHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 131735403HCID 131735403, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDCxHCl (17.7 g, 93.00 mmol, 1.5 eq), 1-hydroxy-7-azabenzotriazole (4.2 g, 31.01 mmol, 0.5 eq) followed by triethylamine (28.7 mL, 204 mmol, 3.3 eq) were added at room temperature to a stirred solution of 1H-indole-6-carboxylic acid (10 g, 62.03 mmol, 1.0 eq) in dry DMF (50 mL). (R)-tert-butyl pyrrolidin-3-ylcarbamate (13.86 g, 74.44 mmol, 1.2 eq) was added after 10 min and stirring was continued for 16 h at room temperature. The reaction mixture was diluted with icy water (100 mL), and the precipitating solid was filtered off, washed with water (50 mL) and pet ether (50 mL), and dried under vacuum. White solid. Yield: 11.0 g (55% of theory)

Workup

  1. filtrationthe precipitating solid was filtered off
  2. washwashed with water (50 mL) and pet ether (50 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-89f1c34a589e4208b58985a8aff49c45
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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