Water → HCID 59807888, compound

HRID 912568Notes

Reaction equation

HRID 912568 reaction equation
C([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:18]=[C:17]([CH3:19])[N:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[C:15]=2[CH3:30])=[O:13])=[CH:7][CH:6]=1)C.O.[OH-].[Li+].O.C1COCC1>CO>[CH3:30][C:15]1[N:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:28])([F:29])[F:27])[C:17]([CH3:19])=[CH:18][C:14]=1[C:12]([NH:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:31])=[O:3])=[CH:10][CH:9]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59807826HCID 59807826, compound

Product 1

HCID 59807888HCID 59807888, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-({2,5-dimethyl-1-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbonyl}-amino)-benzoic acid ethyl ester (0.46 g, 1.1 mmol), lithium hydroxide monohydrate (0.15 g, 3.5 mmol, 3.3 eq), 2 mL of water, 2 mL of THF, and 3 mL of MeOH was stirred 17h and then was concentrated under reduced pressure. The resulting suspension was treated with 200 μL of TFA and was washed into a separatory funnel with DCM and water. The water was separated and extracted with DCM. The combined extracts were dried (Na2SO4) and concentrated in vacuo. The crude acid was purified by reverse-phase HPLC to afford the title compound (65 mg, 15%) as a colorless solid; 1H NMR (DMSO-d6): δ 12.7-12.8 (brs, 1H), 9.84 (s, 1H), 8.12 (d, J=8 Hz, 1H), 8.03 (t, J=8 Hz, 1H), 8.00 (s, 4H), 7.93 (t, J=8 Hz, 1H), 7.61 (d, J=2H), 6.77 (s, 1H), 2.26 (s, 3H), 2.00 (s, 3H); MS (ESI) m/z 403 [M+H]+.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting suspension was treated with 200 μL of TFA
  3. washwas washed into a separatory funnel with DCM and water
  4. customThe water was separated
  5. extractionextracted with DCM
  6. dry with materialThe combined extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude acid was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-f6e4e101e02745aaba7e1ef342d7e39f
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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