Trifluoroacetic acid → HCID 67089008, compound

HRID 1943937Notes

Reaction equation

HRID 1943937 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH2:21][CH3:22])=[N:18][N:17](C(OC(C)(C)C)=O)[C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:30])[C:5]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH2:21][CH3:22])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:30])[C:5]([NH:31][S:32]([CH2:35][CH2:36][CH3:37])(=[O:34])=[O:33])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67089053HCID 67089053, compound

Product 1

HCID 67089008HCID 67089008, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 5-(6-chloro-2-fluoro-3-(propylsulfonamido)benzamido)-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.090 g, 0.162 mmol) and TFA (3.12 mL, 40.5 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure using toluene to azeotrope. The crude material was purified by silica gel flash column chromatography (5% 7N NH3-MeOH in CH2Cl2) to afford 6-chloro-N-(3-ethoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-2-fluoro-3-(propylsulfonamido)benzamide (40 mg, 54% yield). LRMS (ACPI pos) m/e 456.1 (M+1). 1H NMR (400 MHz, d6-DMSO) δ 12.57 (s, 1H), 11.08 (s, 1H), 9.98 (br s, 1H), 8.55 (d, 1H), 8.50 (d, 1H), 7.55 (t, 1H), 7.46 (d, 1H), 4.40 (q, 2H), 3.16 (t, 2H), 1.75 (m, 2H), 1.42 (t, 3H), 0.99 (t, 3H); 19F NMR (376 MHz, DMSO) δ−124.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude material was purified by silica gel flash column chromatography (5% 7N NH3-MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-79701bfb7d8d44b580394d7b7c5dd033
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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