Pyridine → 3-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido-[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5(4H)-one

HRID 1691450Notes

Reaction equation

HRID 1691450 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25](=[N:27][OH:28])[NH2:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:44](OCC)=[O:45]>C(Cl)Cl.CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25]4[NH:26][C:44](=[O:45])[O:28][N:27]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:35])([F:36])[F:34])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 866490386-[(4-tert-Butylphenyl)sulfonyl]-N'-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboximidamide2×

Product 1

HCID 1360812393-[6-[(4-tert-Butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido-[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5(4H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 6-[(4-tert-butylphenyl)sulfonyl]-N′-hydroxy-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carboximidamide (intermediate 55, 0.040 g, 0.0771 mmol) in DCM (0.7 mL) and DMF (1 mL) at 0° C. was added pyridine (7.9 mg, 0.100 mmol) and ethyl chloroformate (8.8 mg, 0.081 mmol), and the reaction was allowed to warm room temperature over 2 h. The volatiles were removed, and the residue was purified by SiO2 column chromatography, eluting with 0-100% EtOAc in hexanes, to yield the desired product. LC/MS: m/e 592.2 (M+H)+.

Workup

  1. customThe volatiles were removed
  2. customthe residue was purified by SiO2 column chromatography
  3. washeluting with 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-2885dd28ddee4c23bd657045ebed6743
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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