HCID 67155778, compound → HCID 67156086, compound

HRID 2196682Notes

Reaction equation

HRID 2196682 reaction equation
[C:1]1([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)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>CO.[Pd]>[CH:1]1([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)[NH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 67155778HCID 67155778, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67156086HCID 67156086, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(3-cyclohexenyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (40 mg, 0.084 mmol) was dissolved in methanol (1 mL), and 10% Pd/C (40 mg, 1 eq.) was then added. This mixture was subjected to 45 psi of hydrogen for 16 hours and filtered through GF/F filter paper. The filtrate was then concentrated. The resulting solids were purified by preparative TLC (2×0.5 mm plates, 10% MeOH/DCM as the eluent) to give N-(3-cyclohexyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (10 mg, 25%). 1H NMR (400 MHz, DMSO-d6) δ 11.34 (s, 1H), 10.82 (s, 1H), 9.79 (br s, 1H), 8.32-8.39 (m, 2H), 7.50-7.56 (m, 1H), 7.19-7.28 (m, 2H), 3.07-3.15 (m, 2H), 2.68-2.78 (m, 1H), 1.96-2.02 (m, 2H), 1.70-1.84 (m, 5H), 1.38-1.49 (m, 4H), 1.21-1.31 (m, 1H), 0.95-1.03 (m, 3H); m/z (APCI-neg) M−1=475.3, (APCI-pos) M+1=477.2.

Workup

  1. filtrationfiltered through GF/F
  2. filtrationfilter paper
  3. concentrationThe filtrate was then concentrated
  4. customThe resulting solids were purified by preparative TLC (2×0.5 mm plates, 10% MeOH/DCM as the eluent)

Sources & evidence

ORD record
ord-d267d5c3bbd849f4ac1eb1648c227afb
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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