Water → HCID 59191300, compound

HRID 626028Notes

Reaction equation

HRID 626028 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])=[C:11]([F:26])[CH:10]=1)(=[O:7])=[O:6].[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.O>C(#N)C>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]([NH:8][S:5]([CH2:4][CH2:3][CH2:2][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)(=[O:7])=[O:6])=[CH:10][C:11]=2[F:26])=[C:17]([O:24][CH3:25])[CH:18]=1)[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 59191294HCID 59191294, compound

Product 1

HCID 59191300HCID 59191300, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-N-[4-(4-ethyl-2-methoxyphenoxy)-3-fluorophenyl]propane-1-sulfonamide (0.38 mmol; 153 mg) in dry acetonitrile (2 mL), under argon, was added morpholine (1.1 mmol; 100 μL). The reaction was heated at 50° C. overnight. After cooling to room temperature, the mixture was hydrolysed with 5 mL of water and extracted with dichloromethane (3*2 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo, the title compound (62 mg; 36%) was obtained after purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—40/60).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with dichloromethane (3*2 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f7701805e04483799864b903f8af653
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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