6-Fluoro-7-(2-fluoro-4-iodo-phenylamino)-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid (2-tert-butoxy-ethoxy)-amide → 6-Fluoro-7-(2-fluoro-4-iodophenylamino)-N-(2-hydroxyethoxy)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamide

HRID 910150Notes

Reaction equation

HRID 910150 reaction equation
C([O:5][CH2:6][CH2:7][O:8][NH:9][C:10]([C:12]1[C:13]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:14]([F:22])[C:15](=[O:21])[N:16]2[C:20]=1[CH2:19][CH2:18][CH2:17]2)=[O:11])(C)(C)C>C(O)(C(F)(F)F)=O>[F:22][C:14]1[C:15](=[O:21])[N:16]2[C:20](=[C:12]([C:10]([NH:9][O:8][CH2:7][CH2:6][OH:5])=[O:11])[C:13]=1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=1[F:31])[CH2:19][CH2:18][CH2:17]2

Participants

3

Reactant 1

HCID 576898066-Fluoro-7-(2-fluoro-4-iodo-phenylamino)-5-oxo-1,2,3,5-tetrahydro-indolizine-8-carboxylic acid (2-tert-butoxy-ethoxy)-amide

Product 1

HCID 426062046-Fluoro-7-(2-fluoro-4-iodophenylamino)-N-(2-hydroxyethoxy)-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxamideYield 60.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 4a (730 mg, 1.33 mmol) was dissolved in TFA (4 mL) and stirred at r.t. for 1 hour. Purification by prep-HPLC gave 393 mg (60%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 11.47 (br s, 1H) 8.06 (br s, 1H) 7.58 (dd, 1H, J=10.7, 1.6 Hz) 7.42 (d, 1H, J=8.8 Hz) 6.80 (td, 1H, J=8.7, 2.8 Hz) 4.01 (t, 2H, J=7.3 Hz) 3.77 (t, 2H, J=4.8 Hz) 3.45 (t, 2H, J=4.8 Hz), 3.18 (t, 2H, J=7.7 Hz) 2.11-2.16 (m, 2H). MS (ES) [m+H] calc'd for C17H16F2IN3O4, 492. found 492.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-f111b6fe5b6c4c999781ec22bb2f7ed4
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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