Ethanolamine → HCID 18343701, compound

HRID 1062379Notes

Reaction equation

HRID 1062379 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([OH:31])=O)=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:38])([F:37])[F:36].[CH2:42]([CH2:44][NH2:45])[OH:43]>CN(C=O)C.C(OCC)(=O)C>[Cl:13][C:14]1[CH:19]=[C:18]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29](=[O:31])[NH:45][CH2:44][CH2:42][OH:43])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH:17]=[CH:16][C:15]=1[NH:32][C:33](=[O:41])[C@:34]([OH:40])([CH3:39])[C:35]([F:37])([F:36])[F:38]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 54539434HCID 54539434, compound

Product 1

HCID 18343701HCID 18343701, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 1,1′-carbonyldiimidazole (0.169 g) and (R)-N-[2-chloro-4-(4-carboxyphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 121) (0.30 g) in DMF (1 ml)/ethyl acetate (9 ml) was heated at 50° C. for 30 minutes. Ethanolamine (0.055 ml) was added and the mixture was heated and stirred a further 17 hours. The mixture was cooled, diluted with ethyl acetate (50 ml), washed with dilute aqueous hydrochloric acid (25 ml), water (25 ml), saturated aqueous sodium hydrogen carbonate solution (25 ml) and brine, then dried. Volatile material was removed by evaporation and the residue was purified by chromatography, eluting with 2.5% methanol/ethyl acetate to give the title compound (0.25 g) as a solid. NMR (CDCl3+DMSO-δ6): 1.58 (s, 3H), 3.44 (m, 2H), 3.62 (m, 2H), 4.26 (t, 1H), 7.05 (s, 1H), 7.76 (dd, 1H), 7.83-8.01 (m, 6H), 8.56 (d, 1H); 9.73 (brs, 1H); MS (ESP−): 495.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled
  3. washwashed with dilute aqueous hydrochloric acid (25 ml), water (25 ml), saturated aqueous sodium hydrogen carbonate solution (25 ml) and brine
  4. customdried
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by chromatography
  7. washeluting with 2.5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-95c68439a3a44db5a1175ffcd7ea6bc7
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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