1,1'-Carbonyldiimidazole → tert-butyl 5-(6-(5-(2,3-dihydro-1H-inden-2-yl)-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927284Notes

Reaction equation

HRID 927284 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]1[C:22]([OH:24])=O.[F:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:41]([CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([C:53](=[N:55]O)[NH2:54])[CH:38]=3)[C:33]2=[O:57])=[CH:28][CH:27]=1>CN(C=O)C>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][CH:14]1[C:22]1[O:24][N:54]=[C:53]([C:37]2[CH:38]=[C:39]3[C:34](=[CH:35][CH:36]=2)[C:33](=[O:57])[N:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[C:41]([CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])=[CH:40]3)[N:55]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 5757772-Indancarboxylic AcidHCID 90095090tert-butyl 5-(2-(4-fluorophenyl)-6-(N'-hydroxycarbamimidoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Product 1

HCID 90095432tert-butyl 5-(6-(5-(2,3-dihydro-1H-inden-2-yl)-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

CDI (21.45 mg, 0.132 mmol) was added to a stirred, room temperature mixture of 2-indanecarboxylic acid (17.88 mg, 0.110 mmol) in DMF (1 mL), and the mixture was stirred at room temperature for 2 h. tert-butyl 5-(2-(4-fluorophenyl)-6-(N′-hydroxycarbamimidoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (50 mg, 0.110 mmol) was added, and the resultant mixture was kept stirring at 100° C. for overnight. The reaction was checked with LCMS and starting material disappeared. The mixture was cooled to room temperature, precipitate formed, filtered and washed with water (20 mL), dried in vacuum oven to give tert-butyl 5-(6-(5-(2,3-dihydro-1H-inden-2-yl)-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (51 mg, 0.088 mmol) as a light tan solid.

Workup

  1. additionwas added
  2. customprecipitate formed
  3. filtrationfiltered
  4. washwashed with water (20 mL)
  5. customdried in vacuum oven

Sources & evidence

ORD record
ord-713b2aca067c4003ba7c66dc9b64d69b
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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