HCID 67088877, compound → HCID 56682215, compound

HRID 1943946Notes

Reaction equation

HRID 1943946 reaction equation
[CH:1]1([CH2:5][O:6][C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17](=[O:33])[C:18]4[C:23]([F:24])=[CH:22][CH:21]=[C:20]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[C:19]=4[F:32])[CH:14]=3)[N:9](CC3C=CC(OC)=CC=3)[N:8]=2)[CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O>[CH:1]1([CH2:5][O:6][C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17](=[O:33])[C:18]4[C:23]([F:24])=[CH:22][CH:21]=[C:20]([NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[C:19]=4[F:32])[CH:14]=3)[NH:9][N:8]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 67088877HCID 67088877, compound

Product 1

HCID 56682215HCID 56682215, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

N-(3-(Cyclobutylmethoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.017 g, 0.028 mmol) was dissolved in TFA (3 mL) and warmed to 50° C. for 16 hours. The mixture was then heated to 70° C. for 3 hours. The reaction mixture was then concentrated under reduced pressure, and the resulting residue was dissolved in DCM (10 mL), washed with saturated sodium bicarbonate solution (2×), dried over sodium sulfate and concentrated under reduced pressure. Preparative TLC (2×0.5 mm plates, 7% MeOH/DCM) afforded N-(3-(cyclobutylmethoxy)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (3 mg, 22%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 8.67-8.62 (m, 1H), 8.56-8.52 (m, 1H), 7.68-7.62 (m, 1H), 7.17-7.10 (m, 1H), 4.39-4.33 (m, 2H), 3.15-3.08 (m, 2H), 2.93-2.82 (m, 1H), 2.22-2.13 (m, 2H), 2.04-1.82 (m, 6H), 1.10-1.02 (m, 3H); m/z (APCI-pos) M+1=480.1.

Workup

  1. temperatureThe mixture was then heated to 70° C. for 3 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in DCM (10 mL)
  4. washwashed with saturated sodium bicarbonate solution (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9463e4a5b3d94010bf07ff49a78c5c52
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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