N-(3-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide → 7-(2-(4-methylpiperazin-1-yl)ethoxy)-N-(1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706743Notes

Reaction equation

HRID 706743 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[N:4]([CH2:33][C:34]2[S:38][C:37]([CH3:39])=[N:36][CH:35]=2)[N:3]=1>CCO.N.CO.C(Cl)Cl.[Pd]>[CH3:32][N:29]1[CH2:28][CH2:27][N:26]([CH2:25][CH2:24][O:23][C:21]2[CH:20]=[CH:19][N:18]3[C:14]([C:12]([NH:11][C:9]4[CH:8]=[CH:7][CH:6]=[C:5]5[C:10]=4[CH:2]=[N:3][N:4]5[CH2:33][C:34]4[S:38][C:37]([CH3:39])=[N:36][CH:35]=4)=[O:13])=[CH:15][N:16]=[C:17]3[CH:22]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 1

HCID 67261270N-(3-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 866993517-(2-(4-methylpiperazin-1-yl)ethoxy)-N-(1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 19.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 21584172Ammonia methanol dichloromethaneSolvent

Procedure

A solution of N-(3-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-methylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide (11.5 mg, 0.018 mmol) in absolute EtOH (1 mL) was treated with Pd/C (Degussa, wet, 10% wt, 2 mg), the reaction flask was flushed with hydrogen, and stirring at ambient temperature was continued for seven hours. The reaction was diluted with DCM, the catalyst was removed by filtration, and the filtrate concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with ammonia/MeOH/DCM as eluent to afford 1.9 mg of the desired product. MS (ES+APCI) m/z=531 (M+H) detected.

Workup

  1. customwet, 10% wt, 2 mg), the reaction flask was flushed with hydrogen
  2. additionThe reaction was diluted with DCM
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate concentrated
  5. customto afford the crude product

Sources & evidence

ORD record
ord-d1f30e1b72ab4d0b9a6612b5a3788e96
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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