Phosphorus sulfide (P2S5) → HCID 58107380, compound

HRID 1970935Notes

Reaction equation

HRID 1970935 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].C([O-])(O)=O.[Na+].[CH:20]1([C:26]2[C:27]3[CH:28]=[CH:29][C:30]([C:45]([O:47][CH3:48])=[O:46])=[CH:31][C:32]=3[N:33]3[C:39]=2[C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[NH:36][C:35](=O)[CH2:34]3)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>O1CCOCC1.O>[CH:20]1([C:26]2[C:27]3[CH:28]=[CH:29][C:30]([C:45]([O:47][CH3:48])=[O:46])=[CH:31][C:32]=3[N:33]3[C:39]=2[C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[NH:36][C:35](=[S:2])[CH2:34]3)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 11494795HCID 11494795, compound

Product 1

HCID 58107380HCID 58107380, compoundYield 165.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

P4S10 (352 mg, 0.791 mmol) and NaHCO3 (554 mg, 6.60 mmol) were added to a solution of methyl 13-cyclohexyl-5H-indolo[1,2-d][1,4]benzodiazepine-6(7H)-one-10-carboxylate (511 mg, 1.32 mmol) in dioxane (10 mL). The reaction mixture was heated at 100° C. for 1 h, cooled to rt, and diluted with the dropwise addition of H2O (˜20 mL) while stirring. The resulting yellow precipitate was allowed to settle for 1 h, collected by filtration, flushed with water and dried under N2 to yield methyl 13-cyclohexyl-5H-indolo[1,2-d][1,4]benzodiazepine-6(7H)-thione-10-carboxylate (528 mg, 1.31 mmol, 99%) as yellow solid, which was used without further purification. LCMS: 405 (M+H)+, ret time 2.26 min.

Workup

  1. temperaturecooled to rt
  2. filtrationcollected by filtration
  3. customflushed with water
  4. customdried under N2

Sources & evidence

ORD record
ord-1a0e6923e13840569a60a746a8858d09
Source dataset
uspto-grants-2013_04
Patent number
US08431568B2

Reaction notes

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