Triethylamine → HCID 59657617, compound

HRID 1866038Notes

Reaction equation

HRID 1866038 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=O)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.ClC(N(C)C)=C(C)C.Cl.Cl.[NH:24]1[CH2:29][CH2:28][C:27]2([C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][NH:30]2)[CH2:26][CH2:25]1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:24]3[CH2:29][CH2:28][C:27]4([C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH2:31][NH:30]4)[CH2:26][CH2:25]3)=[O:13])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 184532356-chloro-1H-indole-3-carboxylic acidHCID 69015598HCID 69015598, compound

Product 1

HCID 59657617HCID 59657617, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.10 g (0.51 mmol) 6-chloro-1H-indole-3-carboxylic acid in 5 ml dichloromethane were added 0.074 ml (0.56 mmol) 1-chloro-N,N,2-trimethyl-propenylamine at room temperature. The reaction mixture was concentrated in vacuo after 1 h. The residue was redissolved in 2 ml dry N,N-dimethylformamide. A suspension of 0.147 g (0.56 mmol) 2,3-dihydrospiro[isoindole-1,4′-piperidine]dihydrochloride and 0.285 ml (2.04 mmol) triethylamine in 2 ml dry N,N-dimethylformamide was added at room temperature. After stirring for 16 h the reaction mixture was quenched with 1 M aqueous sodium hydroxide solution (30 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with water (2×30 ml) and brine (1×30 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (dichloromethane/methanol) to give the title compound (0.045 g; 24%) as an off-white solid. MS m/e (%): 366 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo after 1 h
  2. dissolutionThe residue was redissolved in 2 ml dry N,N-dimethylformamide
  3. additionwas added at room temperature
  4. customwas quenched with 1 M aqueous sodium hydroxide solution (30 ml)
  5. extractionextracted with ethyl acetate (3×50 ml)
  6. washThe combined organic layers were washed with water (2×30 ml) and brine (1×30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-64aac433e7b041b49d888c3b939b43ec
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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