p-Toluenesulfonic acid monohydrate → HCID 59799080, compound

HRID 1013105Notes

Reaction equation

HRID 1013105 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:13][C:14]1[CH:30]=[CH:29][C:17]2[CH2:18][CH2:19][N:20]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:21][CH2:22][C:16]=2[C:15]=1[NH:31][CH2:32][C:33]([CH3:43])([CH3:42])[CH2:34][O:35]C1CCCCO1>CO>[Cl:13][C:14]1[CH:30]=[CH:29][C:17]2[CH2:18][CH2:19][N:20]([C:23](=[O:28])[C:24]([F:26])([F:25])[F:27])[CH2:21][CH2:22][C:16]=2[C:15]=1[NH:31][CH2:32][C:33]([CH3:43])([CH3:42])[CH2:34][OH:35]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57447748HCID 57447748, compound

Product 1

HCID 59799080HCID 59799080, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add p-toluensulfonic acid monohydrate (538 mg, 2.83 mmol) to a solution of 7-chloro-6-[2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.190 g, 2.57 mmol) in methanol (80 mL). Stir the reaction at RT for 16 hr, concentrate, redissolve in EtOAc, wash with saturated aqueous sodium bicarbonate solution, brine, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 1:4 EtOAc:hexanes) to give the title compound (750 mg, 79%).

Workup

  1. customthe reaction at RT for 16 hr
  2. concentrationconcentrate
  3. dissolutionredissolve in EtOAc
  4. washwash with saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdry (sodium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 1:4 EtOAc:hexanes)

Sources & evidence

ORD record
ord-ab53cec2fab248658efc35c4eabbb810
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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