Benzoylhydrazine → HCID 53258710, compound

HRID 1043868Notes

Reaction equation

HRID 1043868 reaction equation
[C:1]1([C:13]([OH:15])=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[C:16]([NH:24][NH2:25])(=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:1]1([C:13]2[O:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:24][N:25]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

3

Reactant 2

HCID 11955BenzoylhydrazineHCID 225568865,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

Product 1

HCID 53258710HCID 53258710, compound

Procedure

2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-5-phenyl-1,3,4-oxadiazole was synthesized as outlined in General Procedure J using 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid and benzohydrazide. The crude product was purified using reverse phase chromatography (HPLC, C-18) using trifluoroacetic acid as a modifier to give the desired product 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-5-phenyl-1,3,4-oxadiazole as a yellow solid. Mp=155-157° C.; 400 MHz 1HNMR (DMSO-d6) δ 8.31 (s, 1H), 8.13-8.10 (m, 2H), 7.90 (d, J=8.0 Hz, 1H), 7.65-7.63 (m, 3H), 7.21 (t, J=6.8 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 4.31 (t, J=5.6 Hz, 2H), 2.99 (t, J=6.0 Hz, 2H), 2.21-2.18 (m, 2H); LCMS [M+H]: 302.

Workup

  1. custom2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-5-phenyl-1,3,4-oxadiazole was synthesized
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-2ca3aa98d6bd48c7868279e8c7ca0e4a
Source dataset
uspto-grants-2013_10
Patent number
US08563567B2

Reaction notes

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