Triethylamine → HCID 68495846, compound

HRID 1038767Notes

Reaction equation

HRID 1038767 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][N:19]4[C:27]5[C:22](=[C:23]([O:28][C:29]6[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][N:30]=6)[CH:24]=[CH:25][CH:26]=5)[CH2:21][CH2:20]4)[CH2:13][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:16][CH2:15][N:14]([C:17](=[O:38])[CH2:18][N:19]4[C:27]5[C:22](=[C:23]([O:28][C:29]6[CH:37]=[CH:36][C:32]([CH2:33][OH:34])=[CH:31][N:30]=6)[CH:24]=[CH:25][CH:26]=5)[CH2:21][CH2:20]4)[CH2:13][CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 68497920HCID 68497920, compound

Product 1

HCID 68495846HCID 68495846, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-{1-[2-(4-Benzo[1,3]dioxol-5-ylmethylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-1H-indol-4-yloxy}nicotinic acid (0.789 g, 1.53 mmol) was suspended in THF (15 mL). To the suspension were added triethylamine 0.234 mL, 1.68 mmol), then ethyl chloroformate (0.161 g, 1.68 mmol) under cooling in an ice-salt bath, and the resulting mixture was stirred for 30 minutes at the same temperature. The reaction mixture was filtered, and to the filtrate was added 80% solution of sodium borohydride (0.289 g, 7.64 mmol) in methanol (20 mL) under cooling with ice, and then the solution was stirred for 30 minutes at the same temperature. The reaction mixture was concentrated and the residue was extracted with ethyl acetate (50 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated to yield 0.671 g of the title compound as a pale brown amorphous powder.

Workup

  1. temperatureunder cooling in an ice-salt bath
  2. filtrationThe reaction mixture was filtered
  3. temperatureunder cooling with ice
  4. stirringthe solution was stirred for 30 minutes at the same temperature
  5. concentrationThe reaction mixture was concentrated
  6. extractionthe residue was extracted with ethyl acetate (50 mL)
  7. washAfter the organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-280bcaab139f4ab28938e53c970c589c
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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