1,1'-Carbonyldiimidazole → HCID 44189273, compound

HRID 656805Notes

Reaction equation

HRID 656805 reaction equation
[CH:1]1([C:4]2[C:5]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([O:18][C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=5)=[CH:14][CH:13]=4)=[C:9]([C:26]([OH:28])=O)[C:8]=3[CH:29]=2)[CH2:3][CH2:2]1.C1N=C[N:37](C(N2C=NC=C2)=O)[CH:36]=1.Cl.CN.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:36][NH:37][C:26]([C:9]1[C:8]2[CH:29]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:5]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:6][C:7]=2[O:11][C:10]=1[C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:28]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 67356068HCID 67356068, compound

Product 1

HCID 44189273HCID 44189273, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 1—To a solution of 28 (0.51 g, 1.07 mmol) in dry DMF (5 mL) was added CDI (0.19 g, 1.17 mmol) and the solution stirred at RT for 2 h. Methyl amine hydrochloride (0.72 g, 10.7 mmol) and DIPEA (1.4 g, 10.7 mmol) were added and the resulting solution heated at 85° C. for 3 h. The solution was cooled and partitioned between EtOAc and H2O. The organic phase was dried (Na2SO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 40% EtOAc) to afford 0.426 g of 5-cyclopropyl-2-[4-(4-fluoro-phenoxy)-phenyl]-6-methanesulfonylamino-benzofuran-3-carboxylic acid methylamide (30).

Workup

  1. temperaturethe resulting solution heated at 85° C. for 3 h
  2. temperatureThe solution was cooled
  3. custompartitioned between EtOAc and H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with an EtOAc/hexane gradient (0 to 40% EtOAc)

Sources & evidence

ORD record
ord-26b8c772810e44f4858b52dcf4ebbcbb
Source dataset
uspto-grants-2011_12
Patent number
US08071797B2

Reaction notes

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