Sodium Iodide → 4-(1H-Indazol-6-ylamino)-6-methoxy-7-(2-morpholine-4-yl-ethoxy)quinoline-3-carbonitrile

HRID 1595813Notes

Reaction equation

HRID 1595813 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([CH:22]=[N:23][NH:24]4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].[I-].[Na+].[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>>[NH:24]1[C:25]2[C:21](=[CH:20][CH:19]=[C:18]([NH:17][C:9]3[C:8]4[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:31]5[CH2:36][CH2:35][O:34][CH2:33][CH2:32]5)=[C:6]([O:27][CH3:28])[CH:7]=4)[N:12]=[CH:11][C:10]=3[C:15]#[N:16])[CH:26]=2)[CH:22]=[N:23]1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 101383914-(1H-Indazol-6-ylamino)-6-methoxy-7-(2-morpholine-4-yl-ethoxy)quinoline-3-carbonitrile

Procedure

The title compound was prepared by the procedure of Example 167 using 0.616 g of 7-(2-chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile, 0.094 g of sodium iodide and 2.03 ml of morpholine to give after purification by chromatography (Silica Gel: ethyl acetate, ethyl acetate/methyl alcohol/triethyl amine 6:4:0.1) 0.196 g (28%) of the desired product. MP 133-135° C. :mass spectrum (electrospray m/e): M+H=445.0.

Workup

  1. customto give
  2. customafter purification by chromatography (Silica Gel: ethyl acetate, ethyl acetate/methyl alcohol/triethyl amine 6:4:0.1) 0.196 g (28%) of the desired product

Sources & evidence

ORD record
ord-ed7c02b7952240a1a3a71d3b986489ab
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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