Sodium Iodide → 7-{2-[(2-hydroxy-ethyl)-amino]-ethoxy}-4(1H-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1595803Notes

Reaction equation

HRID 1595803 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].C[NH:30][CH2:31][CH2:32][OH:33].[I-].[Na+]>COCCOC>[OH:33][CH2:32][CH2:31][NH:30][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]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80162-(Methylamino)ethanolHCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 101367897-{2-[(2-hydroxy-ethyl)-amino]-ethoxy}-4(1H-indazol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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, 375.6 mg (5.0 mmol) of 2-(methylamino)-ethanol and 75.0 mg (0.5 mmol) of sodium iodide in 5 mL of DME was heated at 135° C. for 15 hr. The work up gave 116.4 mg (54.0%) of the product as a yellow solid, m.p. 179° C. (dec.), mass (electrospray, m/e): M+H 433.0.

Sources & evidence

ORD record
ord-165feff1ffc940358f5b3f856602b164
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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