Chlorosuccinimide → HCID 58565361, compound

HRID 2175341Notes

Reaction equation

HRID 2175341 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=[C:17]2[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26])[CH:13]=[CH:14][CH:15]=1>CN(C=O)C.O>[Cl:1][C:18]1[C:19]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([F:9])[CH:11]=2)[C:17]=1[CH:25]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH3:26]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 58565365HCID 58565365, compound

Product 1

HCID 58565361HCID 58565361, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-chlorosuccinimide (24 mg, 0.18 mmol) in DMF (0.1 mL) was added dropwise to an ice-cooled solution of tert-butyl {1-[1-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]ethyl}carbamate (60 mg, 0.17 mmol) (5073-171) in N,N-dimethylformamide (1 mL). The resulting mixture was allowed to warm to room temperature and stirred overnight. The mix was diluted with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified on silica gel (eluting with 0-10% EtOAc/hexane) to give the desired product (26 mg, 40%). LCMS calculated for C20H22ClFN3O2(M+H)+: m/z=390.1. Found: 390.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (eluting with 0-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-b376421636524f1697b701fc495f39c2
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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