4-Methylmorpholine → HCID 54450617, compound

HRID 650664Notes

Reaction equation

HRID 650664 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[Cl-].[C:11]1([S:17]([NH:20][CH:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][NH3+:23])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[C:27]([O:26][C:24](=[O:25])[CH:21]([NH:20][S:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])=[O:18])[CH2:22][NH:23][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9])([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 3491155-Bromothiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757253HCID 86757253, compound

Product 1

HCID 54450617HCID 54450617, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromothiophene-2-carboxylic acid (3.1 g, 15 mmol), 2-benzenesulfonylamino-2-tert-butoxycarbonyl-ethyl-ammonium chloride (4.58 g, 13.6 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.87 g, 15 mmol), 1-hydroxybenzotriazole (2.01 g, 15 mmol) and 4-methylmorpholine (3 mL, 27.3 mmol) in dry dimethylformamide (DMF, 36 mL) was stirred at room temperature for 16 h. The DMF was removed and the mixture was dissolved in ethyl acetate (400 mL), washed with water (25 mL), saturated NaCl solution (25 mL), 5% KHSO4 (25 mL), saturated NaCl solution (25 mL) and saturated NaHCO3-saturated NaCl mixture (1:1) (25 mL), dried and evaporated. The crude was passed through a column of silica gel with CH2Cl2-acetone (95:5 and 90:10) as eluents yielding 6 g of compound A-1(90% yield).

Workup

  1. customThe DMF was removed
  2. dissolutionthe mixture was dissolved in ethyl acetate (400 mL)
  3. washwashed with water (25 mL), saturated NaCl solution (25 mL), 5% KHSO4 (25 mL), saturated NaCl solution (25 mL) and saturated NaHCO3-saturated NaCl mixture (1:1) (25 mL)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-67bb2718fe5e42c28f272c497240b010
Source dataset
uspto-grants-2001_08
Patent number
US06274620B1

Reaction notes

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