Water → HCID 58958618, compound

HRID 915604Notes

Reaction equation

HRID 915604 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[N:15]=[C:14]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C1C(=O)N([I:38])C(=O)C1.O>CC(O)=O.C(Cl)Cl.C(Cl)Cl>[I:38][C:13]1[C:14]([C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[N:15][N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:12]=1[NH:11][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 69275511HCID 69275511, compound

Product 1

HCID 58958618HCID 58958618, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21922555Acetic acid methylene chlorideSolvent

Procedure

To a solution of 5-methyl-2-{[1-(2-methylphenyl)-3-(4-methylphenyl)-1H-pyrazol-5-yl]amino}benzoic acid (Example 65), (49.5 mg, 0.13 mmol) in AcOH/DCM (1:1, v/v) (2 mL) was added a solution of NIS (28 mg, 0.13 mmol) in DCM (1 mL). The reaction was stirred at rt for 3 h. Water (1 mL) was added to the reaction mixture. The water layer was extracted with DCM (2 mL), and the combined organic layers were washed with sodium sulfite and brine, and concentrated under reduced pressure. The crude product was subjected to HPLC purification with a gradient elution from 30% to 95% acetonitrile in water to afford 9.1 mg (14%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 8.88 (s, 1H), 7.85 (d, 2H), 7.74 (s, 1H), 7.18-7.32 (m, 7H), 6.58 (d, 1H), 2.41 (s, 3H), 2.25 (s, 3H), 2.21 (s, 3H). ES-MS m/z 524.1 (MH+); HPLC RT (min) 4.35.

Workup

  1. extractionThe water layer was extracted with DCM (2 mL)
  2. washthe combined organic layers were washed with sodium sulfite and brine
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was subjected to HPLC purification with a gradient elution from 30% to 95% acetonitrile in water

Sources & evidence

ORD record
ord-a7be04091e814f428f6cb99d186e9bad
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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