Ethyl isocyanate → HCID 21099529, compound

HRID 2377018Notes

Reaction equation

HRID 2377018 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:34]([N:36]=[C:37]=[O:38])[CH3:35]>O1CCCC1>[CH2:34]([NH:36][C:37]([NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([C:14]2[CH:13]=[CH:12][C:11](/[CH:10]=[CH:9]/[C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=3)=[CH:16][CH:15]=2)(=[O:19])=[O:18])[CH:21]=1)=[O:38])[CH3:35]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 21099488HCID 21099488, compound

Product 1

HCID 21099529HCID 21099529, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [3-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]amine hydrochloride (Example 212, 100 mg, 0.26 mmol) and triethylamine (0.05 mL, 0.36 mmol) in tetrahydrofuran (2 mL) was cooled to 0° C. and ethyl isocyanate (0.08 mL, 0.31 mmol) added. The reaction was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 40% ethyl acetate/isohexane, followed by trituration with diethyl ether to give the title compound as a white solid (27 mg, 24%). δH (500 MHz, d6 DMSO): 8.85 (1H, s), 8.15 (1H, s), 7.86 (2H, d, J=8.4 Hz), 7.79 (2H, d, J=8.4 Hz), 7.67 (2H, dd, J=5.7, 8.5 Hz), 7.50-7.48 (1H, m), 7.43-7.40 (3H, m), 7.27 (1H, d, J=16.5 Hz), 7.22 (2H, t, J=8.8 Hz), 6.20 (1H, t, J=5.4 Hz), 3.12-3.06 (2H, m), 1.03 (3H, t, J=7.1 Hz).

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-4a02b11d6f2f4bcd8b9352fa5ba0ceef
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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