HCID 44611715, compound → HCID 44611846, compound

HRID 1966865Notes

Reaction equation

HRID 1966865 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:16]([NH:19][CH:20]2[CH2:28][CH2:27][CH2:26][C:25]3[N:24]([CH2:29][C:30]([OH:32])=[O:31])[N:23]=[CH:22][C:21]2=3)(=[O:18])=[O:17])[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1>CO.[Pd]>[F:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[N:6]=[CH:5][C:4]([S:16]([NH:19][CH:20]3[CH2:28][CH2:27][CH2:26][C:25]4[N:24]([CH2:29][C:30]([OH:32])=[O:31])[N:23]=[CH:22][C:21]3=4)(=[O:18])=[O:17])=[CH:3][CH:2]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 44611715HCID 44611715, compound

Product 1

HCID 44611846HCID 44611846, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of {4-[5-bromo-6-(4-fluoro-phenoxy)-pyridine-3-sulfonylamino]-4,5,6,7-tetra-hydro-indazol-1-yl}-acetic acid (example 2-2a) (20 mg, 0.038 mmol) in methanol (5 mL) was hydrogenated over 10% palladium on carbon (2 mg) under 30 psi in a 50 mL parr at room temperature for 3 hours. The mixture was filtered through a glass funnel. The filtrate was concentrated in vacuo and then purified by preparative HPLC to afford {4-[6-(4-fluoro-phenoxy)-pyridine-3-sulfonylamino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid (5 mg, 30%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 8.62 (d, 1 H), 8.28 (dd, 1 H), 7.20 (m, 5 H), 6.87 (s, 1 H), 4.79 (s, 2 H), 4.42 (m, 1 H), 2.57 (m, 2 H), 2.01-1.72 (m, 4 H). MS cald. for C20H19FN4O5S 446, obsd. (ESI+) [(M+H)+] 447.

Workup

  1. filtrationThe mixture was filtered through a glass funnel
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-0f626d6d239c4e50b6f3c3d43ad0d795
Source dataset
uspto-grants-2013_04
Patent number
US08420675B2

Reaction notes

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