Triethylsilane → HCID 18440719, compound

HRID 1455690Notes

Reaction equation

HRID 1455690 reaction equation
C([SiH](CC)CC)C.[Cl:8][C:9]1[S:13][C:12]([C:14]([NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[C:19](=[O:43])[N:20]([CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)[CH:21]3OC)=[O:15])=[CH:11][CH:10]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:8][C:9]1[S:13][C:12]([C:14]([NH:16][C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[C:19](=[O:43])[N:20]([CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH2:21]3)=[O:15])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 18440728HCID 18440728, compound

Product 1

HCID 18440719HCID 18440719, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

0.23 ml (1.4 mmol) of triethylsilane is added to a solution of 378 mg (0.704 mmol) of tert-butyl 4-[2-(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1-methoxy-3-oxo-1,3-dihydro-2H-isoindol-2-yl) ethyl]-1-piperidine carboxylate in 12 ml of dichloromethane and 0.65 ml of trifluoroacetic acid. The mixture is stirred overnight, concentrated and taken up in dichloromethane. The solution is washed with 1N sodium hydroxide solution, dried and concentrated. The residue is crystallized using diethyl ether. The resulting solid is purified further by chromatography on silica gel (gradient from dichloromethane/methanol 95:5 to dichloromethane/methanol/triethylamine 9:1:0.1). Yield: 144 mg (50.5% of theory).

Workup

  1. concentrationconcentrated
  2. washThe solution is washed with 1N sodium hydroxide solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is crystallized
  6. customThe resulting solid is purified further by chromatography on silica gel (gradient from dichloromethane/methanol 95:5 to dichloromethane/methanol/triethylamine 9:1:0.1)

Sources & evidence

ORD record
ord-0b20aa18095e4440b9048a1c41f87ebb
Source dataset
uspto-grants-2009_01
Patent number
US07482472B2

Reaction notes

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