Sodium Iodide → HCID 10185386, compound

HRID 1595807Notes

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

Participants

Reactant 3

HCID 5238Sodium Iodide

HCID 80711,2-Dimethoxyethane

HCID 102940037-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 10185386HCID 10185386, 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, 716.0 mg (5.0 mmol) of 1,4-dioxa-8-azapiro[4,5]decane 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 173.1 mg (69.2%) of the product as aoff white solid, m.p. 245° C. (dec.), mass (electrospray, m/e): M+H 501.0.

Sources & evidence

ORD record: ord-d19db46088744901a677d13bac40400b
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288082B1

Reaction notes

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