2-Methoxyethylamine → HCID 59205420, compound

HRID 2242375Notes

Reaction equation

HRID 2242375 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=1)[C:7]([C:24]([OH:26])=O)=[CH:6]2)#[N:2].S(Cl)(Cl)=O.[CH3:31][O:32][CH2:33][CH2:34][NH2:35].C(N(CC)CC)C>C(Cl)Cl>[CH3:31][O:32][CH2:33][CH2:34][NH:35][C:24]([C:7]1[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:22])([F:23])[F:21])[CH:14]=2)[C:9]2[C:5]([CH:6]=1)=[CH:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=2)=[O:26]

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 685431065-cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid

Product 1

HCID 59205420HCID 59205420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Cyano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (1.00 g, 2.77 mmol) was suspended in anhydrous DCM (20 ml) and thionyl chloride (0.5 ml, 6.85 mmol) added. The reaction was heated under reflux for 3 h then evaporated to dryness. The residue was dissolved in anhydrous DCM and spit into 4 aliquots, one aliquot was added to a solution of methoxyethylamine (0.075 ml, 1.00 mmol) and triethylamine (0.14 ml, 1.00 mmol) in DCM (5 ml). After stirring for 2 h the reaction was washed with water (2 ml) then evaporated to dryness. Crude product was purified by silica chromatography using DCM as eluent then crystallised from DCM:diethyl ether to provide crystalline title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 3 h
  3. customthen evaporated to dryness
  4. dissolutionThe residue was dissolved in anhydrous DCM
  5. washwas washed with water (2 ml)
  6. customthen evaporated to dryness
  7. customCrude product was purified by silica chromatography
  8. customthen crystallised from DCM

Sources & evidence

ORD record
ord-da0ac3e792ba4feea188d62cd366674e
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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