Sodium Iodide → HCID 49839251, compound

HRID 1890028Notes

Reaction equation

HRID 1890028 reaction equation
C[O:2][C:3]1[C:8]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]5[CH2:30][CH2:29][N:28]([CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.[I-].[Na+]>C(O)(=O)C>[CH3:35][N:34]([CH3:36])[C:32](=[O:33])[CH2:31][N:28]1[CH2:29][CH2:30][CH:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:16]3[N:17]=[C:10]4[C:9]([C:8]5[C:3](=[O:2])[NH:4][CH:5]=[CH:6][CH:7]=5)=[CH:14][CH:13]=[CH:12][N:11]4[N:15]=3)=[CH:20][CH:21]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 49839250HCID 49839250, compound

Product 1

HCID 49839251HCID 49839251, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(4-{4-[8-(2-Methoxy-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide (25 mg, 0.052 mmol) in acetic acid (1.3 mL) was added sodium iodide (15.4 mg, 0.103 mmol), and the reaction was stirred at 100° C. for 3 hours. The solvent was evaporated and the residue was diluted with dichloromethane. The dichloromethane solution was washed with 10% sodium thiosulfate solution, brine then dried over sodium sulfate, and concentrated. The product was purified by preparatory TLC (silica gel 10% methanol in dichloromethane) to give the product (13 mg, 54%). MP: >250° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 12.0 (bs, 1H), 9.60 (s, 1H), 8.88 (d, J=6.58 Hz, 1H), 8.75 (d, 1H), 8.45 (d, 1H), 7.70 (d, 2H), 7.50 (m, 1H), 7.20 (m, 2H), 7.05 (t, 1H), 6.45 (t, 1H), 3.25 (s, 2H), 3.05 (s, 3H), 2.90 (m, 2H), 2.78 (s, 3H), 2.45 (m, 1H), 2.10 (m, 2H), 1.85-1.90 (m, 4H). MS=472 (MH)+.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with dichloromethane
  3. washThe dichloromethane solution was washed with 10% sodium thiosulfate solution, brine
  4. dry with materialthen dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by preparatory TLC (silica gel 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-e85700a473694fe0aadbb959948d64b0
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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