Toluene → HCID 9915424, compound

HRID 2406283Notes

Reaction equation

HRID 2406283 reaction equation
[C:1]1([N:7]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8][C@H:9]([NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[N:27]=2)=[CH:20]3)=[O:16])[C:10]([NH:12][NH2:13])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:40](Cl)(Cl)=[O:41].C1(C)C=CC=CC=1>C(Cl)Cl>[C:34]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C@H:9]([NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[N:27]=2)=[CH:20]3)=[O:16])[C:10]2[O:11][C:40](=[O:41])[NH:13][N:12]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 12147836HCID 12147836, compound

Product 1

HCID 9915424HCID 9915424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.384 mmol) of N—((S)-2-diphenylamino-1-hydrazinocarbonylethyl)-2-(2-methylaminopyrimidin-4-yl)-1H-indole-5-carboxamide (12) were suspended in 20 ml of methylene chloride, and a 20% solution of phosgene in toluene (0.398 mmol) was added dropwise at 0° C. and while stirring. The mixture was stirred at room temperature for a further 15 h and the solvent was concentrated. The oxadiazolone 13 was subsequently isolated by flash chromatography on silica gel (DCM:MeOH=9:1). Yield: 160 mg (76%)

Workup

  1. stirringThe mixture was stirred at room temperature for a further 15 h
  2. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-31e84d2b421e43f28b912dc28a9b42ca
Source dataset
uspto-grants-2014_08
Patent number
US08809358B2

Reaction notes

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