Sodium Iodide → 4-[(1H-Indazol-6-yl)amino]-6-methoxy-7-[3-(morpholin-4-yl)propoxy]quinoline-3-carbonitrile

HRID 1595816Notes

Reaction equation

HRID 1595816 reaction equation
ClCCCO[C:6]1[C:15]([C:16]#[N:17])=[C:14]([NH:18][C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][NH:25]3)=[CH:21][CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:28][CH3:29])[CH:12]=2)[N:7]=1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.[I-].[Na+]>COCCOC>[NH:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][C:14]3[C:13]4[C:8](=[CH:9][C:10]([O:28][CH2:11][CH2:10][CH2:9][N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[C:11]([O:28][CH3:29])[CH:12]=4)[N:7]=[CH:6][C:15]=3[C:16]#[N:17])[CH:27]=2)[CH:23]=[N:24]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 21704783HCID 21704783, compound

Product 1

HCID 101829214-[(1H-Indazol-6-yl)amino]-6-methoxy-7-[3-(morpholin-4-yl)propoxy]quinoline-3-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared by the procedure of Example 167 using 0.408 g of (3-chloropropoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile, 1.4 ml of morpholine, 0.060 g of sodium iodide and 12 ml of ethylene glycol dimethyl ether to give 0.255 g (56%) of the desired product. MP 143-145° C.; HRMS: C25H26N6O3: m/z 458.2084; δ(mu)−1.7

Sources & evidence

ORD record
ord-2193de6f394d4d1e918af172a942ed3f
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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