4-Methylmorpholine → HCID 70244919, compound

HRID 650665Notes

Reaction equation

HRID 650665 reaction equation
CN1CCOCC1.[Br:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1.[Cl-].[C:18]([O:22][C:23]([CH:25]([NH:28][S:29]([C:32]1[C:37]([CH3:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=1[CH3:40])(=[O:31])=[O:30])[CH2:26][NH3+:27])=[O:24])([CH3:21])([CH3:20])[CH3:19].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[C:18]([O:22][C:23](=[O:24])[CH:25]([NH:28][S:29]([C:32]1[C:37]([CH3:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=1[CH3:40])(=[O:31])=[O:30])[CH2:26][NH:27][C:14]([C:12]1[S:13][C:9]([Br:8])=[CH:10][CH:11]=1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 3491155-Bromothiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86757254HCID 86757254, compound

Product 1

HCID 70244919HCID 70244919, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methylmorpholine (3.6 mL, 32.7 mmol) was added to a mixture of 5-bromothiophene-2-carboxylic acid (3.6 g; 17.4 mmol), 2-tert-butoxycarbonyl-2-(2,4,6-trimethyl-benzenesulfonylamino)-ethyl-ammonium chloride (6.0 g; 15.85 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.34 g; 17.4 mmol) and 1-hydroxybenzotriazole (2.35 g; 17.4 mmol) in dry DMF (45 mL). The mixture was stirred at room temperature for 16 h. DMF was removed and the crude mixture was dissolved in ethyl acetate (400 mL). The solution was washed with water (25 mL), saturated NaCl (25 mL), 5% KHSO4 (25 mL), saturated NaCl (25 mL), saturated NaHCO3-saturated NaCl mixture (1:1) (25 mL), dried and evaporated. The crude was passed through a column of silica gel and the column was eluted with hexane-EtOAc mixtures (10% to 30% EtOAc) yielding 7.9 g of compound A-2 containing trace amount of ethyl acetate (90% yield).

Workup

  1. customDMF was removed
  2. dissolutionthe crude mixture was dissolved in ethyl acetate (400 mL)
  3. washThe solution was washed with water (25 mL), saturated NaCl (25 mL), 5% KHSO4 (25 mL), saturated NaCl (25 mL), saturated NaHCO3-saturated NaCl mixture (1:1) (25 mL)
  4. customdried
  5. customevaporated
  6. washthe column was eluted with hexane-EtOAc mixtures (10% to 30% EtOAc)

Sources & evidence

ORD record
ord-c64d4b2142a6491b8d880484fca75872
Source dataset
uspto-grants-2001_08
Patent number
US06274620B1

Reaction notes

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