Trifluoroacetic acid → HCID 67156037, compound

HRID 2196675Notes

Reaction equation

HRID 2196675 reaction equation
[F:1][C:2]1[C:41]([NH:42][S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])=[CH:40][CH:39]=[C:38]([F:49])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH:17]=3)[N:13]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:10]2=[N:11][CH:12]=1)=[O:5].FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[C:41]([NH:42][S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])=[CH:40][CH:39]=[C:38]([F:49])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH:17]=3)[N:13]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:30])=[O:31])[C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67156136HCID 67156136, compound

Product 1

HCID 67156037HCID 67156037, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(5-(2,6-difluoro-3-(propylsulfonamido)benzamido)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (50 mg, 0.07 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (3 mL). After 2 hours, the volatiles were removed under reduced pressure, and the residue was partitioned between EtOAc and saturated NaHCO3. The organic layer was dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography (eluting with 90:10:1 CH2Cl2/MeOH/NH4OH) to afford 2,6-difluoro-N-(1-(phenylsulfonyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (29 mg, 67%) as a solid.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and saturated NaHCO3
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (eluting with 90:10:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-8b76d4b98da1485588aecdf747295001
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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