HCID 67156141, compound → HCID 67156073, compound

HRID 2196679Notes

Reaction equation

HRID 2196679 reaction equation
[CH3:1][N:2]([CH3:33])[CH2:3][C:4]#[C:5][C:6]1[NH:32][C:9]2=[N:10][CH:11]=[C:12]([NH:14][C:15](=[O:31])[C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[C:17]=3[F:30])[CH:13]=[C:8]2[CH:7]=1.[H][H]>CO.[Pd]>[CH3:33][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[NH:32][C:9]2=[N:10][CH:11]=[C:12]([NH:14][C:15](=[O:31])[C:16]3[C:21]([F:22])=[CH:20][CH:19]=[C:18]([NH:23][S:24]([CH2:27][CH2:28][CH3:29])(=[O:26])=[O:25])[C:17]=3[F:30])[CH:13]=[C:8]2[CH:7]=1

Participants

5

Reactant 2

HCID 67156141HCID 67156141, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67156073HCID 67156073, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(2-(3-(dimethylamino)prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (30 mg, 63 mmol) in MeOH (10 mL) was treated with 10% Pd/C and allowed to stir under a balloon atmosphere of hydrogen for 4 hours. The mixture was filtered through GF/F paper, rinsing with MeOH. The filtrate was purified by silica gel chromatography (eluting with 10% MeOH/DCM containing 1% NH4OH) to afford N-(2-(3-(dimethylamino)propyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (13 mg, 27 mmol, 43%) as a solid. 1H NMR (400 MHz, d6-DMSO) δ 11.50 (s, 1H), 10.77 (s, 1H), 9.80 (br s, 1H), 8.27-8.18 (m, 2H), 7.56-7.49 (m, 1H), 7.26-7.20 (m, 1H), 6.19-6.17 (m, 1H), 3.12-3.08 (m, 2H), 2.76-2.71 (m, 2H), 2.32-2.27 (m, 2H), 2.17 (s, 6H), 1.87-1.72 (m, 2H), 1.01-0.97 (m, 3H); m/z (APCI-pos) M+1=480.1.

Workup

  1. filtrationThe mixture was filtered through GF/F paper
  2. washrinsing with MeOH
  3. customThe filtrate was purified by silica gel chromatography (eluting with 10% MeOH/DCM containing 1% NH4OH)

Sources & evidence

ORD record
ord-bc959ae27bcd46a19710d9e683462a73
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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