Ethanolamine → HCID 86587514, compound

HRID 2296683Notes

Reaction equation

HRID 2296683 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:16][C:15]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26](OC4C=CC=CC=4)=[O:27])[CH2:22][C@@H:21]3[C:35]([NH:37][O:38][CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][O:40]3)=[O:36])(=[O:19])=[O:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>CN(C=O)C>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:16][C:15]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]([NH:1][CH2:2][CH2:3][OH:4])=[O:27])[CH2:22][C@@H:21]3[C:35]([NH:37][O:38][CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][O:40]3)=[O:36])(=[O:19])=[O:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 54521784HCID 54521784, compound

Product 1

HCID 86587514HCID 86587514, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Aminoethanol (129 mg) was added to a solution of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-4-phenoxycarbonyl-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (250 mg) in DMF (2 ml). The reaction mixture was stirred at 80° C. overnight. The mixture was concentrated in vacuo, and the residue was partitioned between AcOEt and H2O. The organic layer was washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated in vacuo. The residue was purified by SiO2 column chromatography eluted with MeOH in CHCl3=2%, then 4%, to give 138 mg of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-4-[N-(2-hydroxyethyl)-aminocarbonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between AcOEt and H2O
  3. washThe organic layer was washed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 column chromatography
  7. washeluted with MeOH in CHCl3=2%

Sources & evidence

ORD record
ord-a86e63bc811a483e8fb64703c1c73c46
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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