Ethanolamine → [2-(2-Hydroxyethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate

HRID 1399991Notes

Reaction equation

HRID 1399991 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][C:8]([O:17][S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[CH:7][C:5]=2[N:6]=1.[CH:25]1N=C[N:27]([C:30](N2C=NC=C2)=[O:31])[CH:26]=1.C(CN)[OH:38]>CN(C=O)C.CCOC(C)=O>[OH:38][CH2:25][CH2:26][NH:27][C:30]([NH:1][C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][C:8]([O:17][S:18]([C:21]([F:23])([F:22])[F:24])(=[O:20])=[O:19])=[CH:7][C:5]=2[N:6]=1)=[O:31]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 86696901[2-Amino-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate

Product 1

HCID 86696902[2-(2-Hydroxyethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]trifluoromethanesulfonateYield 46.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Compound i (445 mg, 1.18 mmol) was dissolved in DMF (7 mL) and solution of CDI (577 mg, 3.56 mmol) in DMF (3 mL) was added drop-wise at 0° C. with stirring under argon. The mixture was warmed to RT and stirred for 16 h. A solution of ethanolamine (710 μL, 11.85 mmol) in DMF (2 mL) was then added and the mixture stirred at RT for 4 h. The mixture was diluted with EtOAc, washed with H2O, brine. The organic fraction was dried (Na2SO4) and concentrated in vacuo. The residue was washed with MeOH and Et2O to afford ii (253 mg, 46%). MS: 463.00 [M+H]+.

Workup

  1. stirringstirred for 16 h
  2. stirringthe mixture stirred at RT for 4 h
  3. washwashed with H2O, brine
  4. dry with materialThe organic fraction was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with MeOH and Et2O

Sources & evidence

ORD record
ord-7deed7ad5c114db5819545290252282d
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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