4-t-Butylbenzenesulfonyl chloride → 8-Iodo-6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

HRID 1691438Notes

Reaction equation

HRID 1691438 reaction equation
BrC1C=CC2NC3N=C(C(F)(F)F)C=CC=3CN(S(C3C=CC(C(C)(C)C)=CC=3)(=O)=O)C=2C=1.[I:34][C:35]1[CH:36]=[CH:37][C:38]2[NH:44][C:43]3[N:45]=[C:46]([C:49]([F:52])([F:51])[F:50])[CH:47]=[CH:48][C:42]=3[CH2:41][NH:40][C:39]=2[CH:53]=1.BrC1C=CC2NC3N=C(C(F)(F)F)C=CC=3CNC=2C=1.[F:74][C:75]([F:88])([F:87])[O:76][C:77]1[CH:82]=[CH:81][C:80]([S:83](Cl)(=[O:85])=[O:84])=[CH:79][CH:78]=1.C(C1C=CC(S(Cl)(=O)=O)=CC=1)(C)(C)C>>[I:34][C:35]1[CH:36]=[CH:37][C:38]2[NH:44][C:43]3[N:45]=[C:46]([C:49]([F:52])([F:50])[F:51])[CH:47]=[CH:48][C:42]=3[CH2:41][N:40]([S:83]([C:80]3[CH:79]=[CH:78][C:77]([O:76][C:75]([F:74])([F:87])[F:88])=[CH:82][CH:81]=3)(=[O:85])=[O:84])[C:39]=2[CH:53]=1

Participants

6

Reactant 5

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 596186368-bromo-6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepineHCID 669015968-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine2×HCID 669016538-bromo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Product 1

HCID 596187318-Iodo-6-{[4-(trifluoromethoxy)phenyl]sulfonyl}-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine

Procedure

The title compound was prepared following the procedure described for intermediate 53 substituting 8-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 37) for 8-bromo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine, and 4-(trifluoromethoxy)benzenesulfonyl chloride substituted for [(4-tert-butylphenyl)-sulfonyl chloride. LC/MS: m/e 615.8 (M+H)+. 1H NMR (500 MHz, acetone-d6): δ 7.80 (1H, d, J=2.0 Hz), 7.79 (1H, d, J=7.8 Hz), 7.66 (1H, dd, J=8.5, 2.0 Hz), 7.55 (2H, d, J=8.4 Hz), 7.29 (2H, d, J=8.2 Hz), 7.17 (1H, d, J=7.6 Hz), 7.15 (2H, d, J=8.6 Hz), 4.70-4.90 (2H, br).

Sources & evidence

ORD record
ord-469482c4e523431ca2e8ec4cbca94483
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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