Sodium Iodide → HCID 24769328, compound

HRID 1889275Notes

Reaction equation

HRID 1889275 reaction equation
C([O:3][C:4]([C:6]1([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1>CN(C=O)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([O:35][CH2:34][CH2:33][O:23][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:21]=[CH:22][C:13]=2[C:11]([NH:10][C:6]2([C:4]([OH:3])=[O:5])[CH2:7][CH2:8][CH2:9]2)=[O:12])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 59707047HCID 59707047, compound

Product 1

HCID 24769328HCID 24769328, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 94 mg 1-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-cyclobutanecarboxylic acid ethyl ester, 195 mg cesium carbonate and 5 mg sodium iodide in 3 ml of abs. DMF 78 mg of 4-Chlorphenyl 2-bromoethyl ether were added. The reaction mixture was stirred for 2 h at room temperature, then for 5 h at 80° C. The cooled reaction mixture was filtrated, and the filtrate was diluted with 20 ml ethyl acetate and washed twice with brine. The organic phase was concentrated in vacuo, and the resulting residue was dissolved in 2 ml methanol and 1 ml THF. After addition of 0.75 ml 2M NaOH (aq) the mixture was stirred for 1 h at 45° C. and then overnight at room temperature. The solution was neutralized with 0.75 ml 2 M hydrochloride acid, evaporated, and the resulting residue was purified by RP-HPLC to yield 42 mg 1-({1-[2-(4-chloro-phenoxy)-ethoxy]-naphthalene-2-carbonyl}-amino)-cyclobutanecarboxylic acid.

Workup

  1. waitfor 5 h at 80° C
  2. customThe cooled reaction mixture
  3. filtrationwas filtrated
  4. additionthe filtrate was diluted with 20 ml ethyl acetate
  5. washwashed twice with brine
  6. concentrationThe organic phase was concentrated in vacuo
  7. dissolutionthe resulting residue was dissolved in 2 ml methanol
  8. additionAfter addition of 0.75 ml 2M NaOH (aq) the mixture
  9. stirringwas stirred for 1 h at 45° C.
  10. customovernight
  11. customat room temperature
  12. customevaporated
  13. customthe resulting residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-d4b767ce28644294b0ea9390490b8571
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…