Hydrochloric Acid → HCID 66901786, compound

HRID 1691451Notes

Reaction equation

HRID 1691451 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]([NH:27][NH2:28])=[O: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].[CH2:37](OC(OCC)OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>>[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[O:26][CH:37]=[N: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

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 669016526-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide2×

Product 1

HCID 66901786HCID 66901786, compound

Procedure

A mixture of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbohydrazide (intermediate 57, 0.023 g, 0.0443 mmol), triethylorthoformate (0.25 mL), and p-toluenesulfonic acid (5 mg) was stirred at rt for 2 h. Aqueous 1N HCl was added and stirring continued for 45 min. The reaction was quenched with saturated aqueous NaHCO3, and the product was extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4) and concentrated. The residue was purified by SiO2 column chromatography to afford the title compound. LC/MS: m/e 530.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.5 (1H, s), 8.28 (1H, d, J=2.1 Hz), 8.06 (1H, dd, J=8.7, 2.0 Hz), 7.64 (1H, d, J=7.6 Hz), 7.16 (1H, d, J=7.5 Hz), 7.13 (2H, d, J=8.5 Hz), 7.04 (1H, s), 6.95 (2H, d, J=8.4 Hz), 6.91 (1H, d, J=8.5 Hz), 4.70-4.59 (2H, br), 1.26 (9H, s).

Workup

  1. stirringstirring
  2. waitcontinued for 45 min
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. extractionthe product was extracted with EtOAc
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-7c46941bb46d4541b61f4350d05ce884
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

Loading…