3-Oxabicyclo(3.1.0)hexane-2,4-dione → cis-2-{[1-(2-Fluorobenzyl)-7-(2-{[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}ethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid

HRID 82858Notes

Reaction equation

HRID 82858 reaction equation
[NH2:1][C@H:2]1[C@@H:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]2[CH:9]=[C:8]([O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]3[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=3)(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[CH:33]12[CH2:38][CH:37]1[C:36](=[O:39])[O:35][C:34]2=[O:40]>CN(C)C=O>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:20][CH2:21][CH2:22][NH:23][S:24]([C:27]3[N:28]=[CH:29][N:30]([CH3:32])[CH:31]=3)(=[O:26])=[O:25])[CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:1][C:36]([C@H:37]1[CH2:38][C@H:33]1[C:34]([OH:40])=[O:35])=[O:39]

Participants

4

Reactant 2

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 86685677cis-N-(2-{[7-Amino-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Product 1

HCID 86685676cis-2-{[1-(2-Fluorobenzyl)-7-(2-{[(1-methyl-1H-imidazol-4-yl)sulfonyl]amino}ethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamoyl}cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

cis-N-(2-{[7-Amino-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide (50 mg, 0.109 mmol) was dissolved in dimethylformamide (2 mL), 3-oxabicyclo[3.1.0]hexane-2,4-dione (13.4 mg 0.12 mmol) was added and the reaction mixture was heated to 110° C. for 2 h. The solvent was removed in vacuo and the crude product was taken up in dichloromethane and washed successively with water (2×) and saturated sodium chloride solution (1×) and dried (magnesium sulfate). The solvent was evaporated in vacuo and the crude product was used for the next step without further purification. Yield: 63 mg (colorless foam).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed successively with water (2×) and saturated sodium chloride solution (1×)
  3. dry with materialdried (magnesium sulfate)
  4. customThe solvent was evaporated in vacuo
  5. customthe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-369c81d96c3048c7af50d470364dba86
Source dataset
uspto-grants-2014_09
Patent number
US08846741B2

Reaction notes

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