Cesium carbonate → Methyl 4-{[cyclopentyl(4-{[2-(2-methylpropyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]-methyl}phenyl)acetyl]amino}-2,3-dihydro-1H-indene-2-carboxylate

HRID 877182Notes

Reaction equation

HRID 877182 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:10]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]3)=[O:11])=[CH:5][CH:4]=1.[CH3:31][CH:32]([CH3:41])[CH2:33][C:34]1[O:35][CH2:36][C:37](=[O:40])[NH:38][N:39]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:26]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:38]3[C:37](=[O:40])[CH2:36][O:35][C:34]([CH2:33][CH:32]([CH3:41])[CH3:31])=[N:39]3)=[CH:4][CH:5]=2)[C:10]([NH:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17]3)=[O:11])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 581365582-(2-methylpropyl)-4H-1,3,4-oxadiazin-5(6H)-oneHCID 58136756Methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 58136403Methyl 4-{[cyclopentyl(4-{[2-(2-methylpropyl)-5-oxo-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl]-methyl}phenyl)acetyl]amino}-2,3-dihydro-1H-indene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.213 mmol) of methyl 4-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2,3-dihydro-1H-indene-2-carboxylate were dissolved in 3.5 ml of DMF, and 55 mg (0.213 mmol) of 2-(2-methylpropyl)-4H-1,3,4-oxadiazin-5(6H)-one (Example 22A) and 76 mg (0.234 mmol) of cesium carbonate were added. The reaction mixture was stirred at room temperature for 3 d. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by preparative HPLC. This gave 8 mg (8% of theory) of the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7917be37c8f54eeaaedb1a901b0bb836
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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