Trifluoroacetic acid → {3-[6-[(4-tert-Butylphenyl)sulfonyl]-10-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5-yl}methanol

HRID 1691460Notes

Reaction equation

HRID 1691460 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]4[N:29]=[C:28]([CH2:30][OH:31])[O:27][N:26]=4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:32]=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:34]=[CH:35][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[I:40]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(Cl)Cl>[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]4[N:29]=[C:28]([CH2:30][OH:31])[O:27][N:26]=4)[CH:23]=[C:24]([I:40])[C:19]=3[NH:18][C:17]3[N:32]=[C:33]([C:36]([F:38])([F:37])[F:39])[CH:34]=[CH:35][C:16]=3[CH2:15]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 59618782{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-yl}methanol

Product 1

HCID 59618761{3-[6-[(4-tert-Butylphenyl)sulfonyl]-10-iodo-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]-1,2,4-oxadiazol-5-yl}methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {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-yl}methanol (Example 437, 49 mg, 0.0877 mmol) (1.5 mL) and N-iodosuccinimide (21 mg) in DCM at 0° C. was added trifluoroacetic acid (30 mg, 0.263 mmol). After stirring for 2 h, the reaction was quenched with 10% aqueous Na2S2O3 and the product was extracted with EtOAc. The combined extracts were washed with water, brine, dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography, eluting with 50% EtOAc in hexanes, to provide the title compound. LC/MS: m/e 586.0 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.55 (1H, d, J=1.8 Hz), 8.32 (1H, d, J=1.8 Hz), 7.64 (1H, d, J=7.6 Hz), 7.28 (1H, s), 7.20 (1H, J=7.5 Hz), 7.13 (2H, J=8.4 Hz), 6.86 (2H, J=8.5 Hz), 5.02 (2H, s), 4.30-5.0 (2H, br), 2.75 (1H, s br), 1.30 (9H, s).

Workup

  1. customthe reaction was quenched with 10% aqueous Na2S2O3
  2. extractionthe product was extracted with EtOAc
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by SiO2 column chromatography
  7. washeluting with 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-4a916b262e6848c9b4c2c42db45dcab5
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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