Ethanolamine → HCID 69752227, compound

HRID 1062365Notes

Reaction equation

HRID 1062365 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[Cl:5][C:6]1[CH:11]=[C:10]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2F)(=[O:14])=[O:13])[CH:9]=[CH:8][C:7]=1[NH:22][C:23](=[O:31])[C@:24]([OH:30])([CH3:29])[C:25]([F:28])([F:27])[F:26].[Cl-].[NH4+]>CN1C(=O)CCC1>[Cl:5][C:6]1[CH:11]=[C:10]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[NH:4][CH2:3][CH2:1][OH:2])(=[O:14])=[O:13])[CH:9]=[CH:8][C:7]=1[NH:22][C:23](=[O:31])[C@:24]([OH:30])([CH3:29])[C:25]([F:28])([F:27])[F:26]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 25517Ammonium ChlorideHCID 54162932HCID 54162932, compound

Product 1

HCID 69752227HCID 69752227, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

Ethanolamine (0.014 ml) was added to a solution of (R)-N-[2-chloro-4-(2-fluoro-phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 63) (0.10 g) in NMP (1.5 ml) and the solution was heated at 120° C. for 18 hours then cooled. Saturated aqueous ammonium chloride solution (10 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-50% ethyl acetate/hexane to give the title compound (0.074 g) as a solid. Mp 68-70° C.; NMR (CDCl3): 1.75 (s, 3H), 3.3 (q, 2H), 3.90 (m, 2H), 3.95 (brs, 1H), 6.50 (brt, 1H), 6.70 (d, 1H) 6.80 (m, 1H), 7.4 (m, 1H), 7.85 (m, 2H), 8.00 (d, 1H), 8.55 (d, 1H), 9.25 (brs, 1H); MS (ESP−): 465; EA: found: C, 46.6; H, 4.0; N, 5.8%; C18H18ClF3N2O5S requires: C, 46.31; H, 3.89; N, 6.00%.

Workup

  1. temperaturethen cooled
  2. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  3. washwashed with brine
  4. customdried
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  7. washeluting with 0-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-b2595801ba8640cab273352cd9668da8
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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