Triethylamine → HCID 9950997, compound

HRID 2376912Notes

Reaction equation

HRID 2376912 reaction equation
Cl.[NH:2]1[CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:13][NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([N:33](C(OC4C=CC=CC=4)=O)[C:34](=O)[O:35]C4C=CC=CC=4)[CH:28]=3)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1)=[O:16]>CN(C)C=O>[CH3:13][NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][C:22]([O:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([NH:33][C:34]([N:2]4[CH2:5][CH2:4][CH2:3]4)=[O:35])[CH:28]=3)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12308726Azetidine hydrochlorideHCID 21949175Phenyl N-(4-(1-(methylamino)carbonyl-1H-5-indolyloxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate

Product 1

HCID 9950997HCID 9950997, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Azetidine hydrochloride (104 mg, 1.11 mmol) and triethylamine (0.155 ml, 1.11 mmol) were added to a dimethylformamide (1 ml) solution of phenyl N-(4-(1-(methylamino)carbonyl-1H-5-indolyloxy)-2-pyridyl)-N-(phenoxycarbonyl)carbamate (116 mg, 0.222 mmol) synthesized in Production example 5-2; and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a solvent mixture of ether-hexane=1:1; and the resultant solid was filtered off to yield the title compound (50 mg) as crystals.

Workup

  1. customsynthesized in Production example 5-2
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with a solvent mixture of ether-hexane=1:1
  6. filtrationand the resultant solid was filtered off

Sources & evidence

ORD record
ord-a0e59b567aee47f4bb74dbb1d4fb26a7
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…