Sodium Iodide → HCID 17903651, compound

HRID 1595806Notes

Reaction equation

HRID 1595806 reaction equation
ClCCO[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].[OH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[I-].[Na+].C[O:41][CH2:42][CH2:43]OC>>[OH:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:43][CH2:42][O:41][C:11]2[C:10]([C:15]#[N:16])=[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:8]3[C:13](=[CH:14][CH:5]=[C:6]([O:27][CH3:28])[CH:7]=3)[N:12]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 76771-(2-Hydroxyethyl)piperazineHCID 80711,2-DimethoxyethaneHCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 17903651HCID 17903651, compound

Conditions

Temperature
135 °C

Procedure

Using an analogous procedure to that described in Example 157, 196.5 mg (0.5 mmol) of the 7-(2-chloro-ethoxy)-4-(1H-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile, 651.0 mg (5.0 mmol) of 1-(2-hydroxyethyl)piperazine and 75.0 mg (0.5 mmol) of sodium iodide in 5 mL of DME was heated at 135° C. for 16 hr. The work up gave 90.5 mg (37.1%) of the product as a yellow solid, m.p. 174° C. (dec.), mass (electrospray, m/e): M+H 488.0.

Sources & evidence

ORD record
ord-82beafa3f19b40e4988aa4116d23c7a7
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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