Azetidine → HCID 58900220, compound

HRID 642680Notes

Reaction equation

HRID 642680 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[C:6]1[C:22](=[O:27])[O:23][C:24](=[O:26])[CH2:25][C:5]2=1.[NH:28]1[CH2:31][CH2:30][CH2:29]1>C(Cl)Cl>[N:28]1([C:24](=[O:26])[CH2:25][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[N:7]([CH2:11][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[C:6]=2[C:22]([OH:23])=[O:27])[CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 86613188HCID 86613188, compound

Product 1

HCID 58900220HCID 58900220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-9-naphthalen-1-ylmethyl-4,9-dihydro-pyrano[3,4-b]indole-1,3-dione (1.0 mmole) in CH2Cl2 (3 ml) was added azetidine(5 mmole) and stirring was continued at 22° C. until completion of the reaction. The mixture was evaporated and the residue partitioned between aqueous HCl and AcOEt. The organic layer was dried, evaporated and the residue triturated with diethylether to give 3-(2-azetidin-1-yl-2-oxo-ethyl)-5-fluoro-1-naphthalen-1-ylmethyl-1H-indole-2-carboxylic acid as a white solid. MS: 417.4 ([M+H]+).

Workup

  1. customwas continued at 22° C. until completion of the reaction
  2. customThe mixture was evaporated
  3. customthe residue partitioned between aqueous HCl and AcOEt
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue triturated with diethylether

Sources & evidence

ORD record
ord-19e48edaafed43eabf38ec6ee9a4c17d
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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