1,1'-Carbonyldiimidazole → HCID 21099508, compound

HRID 2376975Notes

Reaction equation

HRID 2376975 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C:29](N1C=CN=C1)([N:31]1C=CN=C1)=O.Cl.CN>CN1CCCC1=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([NH:31][CH3:29])=[O:25])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6364545Methylamine hydrochlorideHCID 21099506HCID 21099506, compound

Product 1

HCID 21099508HCID 21099508, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)benzoic acid (Example 69,40 mg, 0.1 mmol) in 1-methyl-2-pyrrolidinone (0.3 mL) was added 1,1′-carbonyldiimidazole (19.5 mg, 0.12 mmol). After stirring for 30 minutes, methylamine hydrochloride (8.1 mg, 0.12 mmol) was added and the reaction stirred for 4 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 10% ethanol/ethyl acetate, to give the title compound. δH (500 MHz, d6 DMSO): 8.63 (1H, d, J=4.5 Hz), 8.04-7.94 (6H, m), 7.88-7.82 (3H, m), 7.42-7.34 (2H, m), 7.32-7.26 (1H, m), 7.14 (1H, td, J=1.9, 8.4 Hz), 2.76 (3H, d, J=4.5 Hz); m/z (ES+) 414 [MH+].

Workup

  1. stirringthe reaction stirred for 4 hours
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 10% ethanol/ethyl acetate

Sources & evidence

ORD record
ord-5613be05e5b740f88f42f04afcde26fb
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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