Sodium Iodide → HCID 21106435, compound

HRID 1817120Notes

Reaction equation

HRID 1817120 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH:24]([CH3:26])[N:23]([C:27](=[O:29])[CH3:28])[CH:22]([CH3:30])[CH2:21]4)[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.Cl[CH2:32][CH2:33][O:34][CH2:35][CH2:36]Cl.[I-].[Na+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:26][CH:24]1[CH2:25][N:20]([C:16]2[CH:15]=[C:14]([N:11]3[CH:12]=[N:13][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([N:1]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[CH:3][CH:4]=4)=[N:10]3)[CH:19]=[CH:18][N:17]=2)[CH2:21][CH:22]([CH3:30])[N:23]1[C:27](=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 21106440HCID 21106440, compound

Product 1

HCID 21106435HCID 21106435, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg of 1-(4-{4-[3-(4-Amino-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-yl}-2,6-dimethyl-piperazin-1-yl)-ethanone (0.246 mMol, 1.00 equiv) in 2 mL of DMF was added 100 μL of 2-chloroethyl ether, 50 mg of sodium iodide and 100 mg of K2CO3. After 3 hr at 110° C. the reaction was concentrated and purified by flash chromatography (EtOAc) to yield 70 mg of 1-(2,6-Dimethyl-4-{4-[3-(4-morpholin-4-yl-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-yl}-piperazin-1-yl)-ethanone (0.147 mMol, 59.8% yield). 1H NMR (500 MHz, DMSO-d6) ∂ 9.26 (1H, s), 9.21 (1H, s), 8.20 (1H, d), 7.52 (2H, d), 7.21 (1H, s), 7.12 (1H, d), 6.90 (2H, d), 4.30 (2H, m), 4.05 (2H, m), 3.73 (4H, m), 3.09 (2H, m), 2.99 (4H, m), 2.51 (3H, s), 1.2 (6H, m) ppm. LC/MS: 1.78 min/477.3 (M+1).

Workup

  1. concentrationAfter 3 hr at 110° C. the reaction was concentrated
  2. custompurified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-816b49483a944820aa9e59ba5c5a9d34
Source dataset
uspto-grants-2009_10
Patent number
US07598245B2

Reaction notes

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