Hydrochloric Acid → HCID 66901628, compound

HRID 1691435Notes

Reaction equation

HRID 1691435 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]([O:27]C)=[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].O.Cl.[OH-].[Na+]>C(O)(=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]([OH:27])=[O:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:29]=[C:30]([C:33]([F:35])([F:34])[F:36])[CH:31]=[CH:32][C:16]=3[CH2:15]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66901654HCID 66901654, compound2×

Product 1

HCID 66901628HCID 66901628, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido-[2,3-b][1,5]benzodiazepine-8-carboxylate (90 mg, intermediate 56), water (0.63 mL), conc. HCl (1.25 mL), and glacial acetic acid (2.0 mL) was heated at 130° C. for 2 h. After cooling to rt, 4N aqueous NaOH was added until pH=6. The reaction mixture was extracted with DCM (3×), and the extracts were dried, filtered, and concentrated to provide the title compound. LC/MS: m/e 506.1 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 8.12 (1H, s), 7.79 (1H, dd, J=8.5, 1.6 Hz), 7.49 (1H, d, J=7.5 Hz), 6.99 (3H, m), 6.79 (3H, m), 4.45-4.70 (2H, br), 1.11 (9H, s).

Workup

  1. temperatureAfter cooling to rt
  2. extractionThe reaction mixture was extracted with DCM (3×)
  3. customthe extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38a9522182ca447badfed209ab9640cc
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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