5-Amino-2-methylindole → 6-Cyano-4-(2-methylindol-5-ylamino)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline hydrochloride

HRID 2222429Notes

Reaction equation

HRID 2222429 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:33])=[CH:27]2>>[ClH:1].[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[N:5]=[CH:4][CH:3]=[C:2]2[NH:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]([CH3:33])=[CH:27]2)#[N:13]

Participants

3

Reactant 2

HCID 27339925-Amino-2-methylindoleHCID 597122344-Chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline

Product 1

HCID 691825686-Cyano-4-(2-methylindol-5-ylamino)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline hydrochlorideYield 39.6%

Procedure

Using an analogous procedure to that described in Example 33, 4-chloro-6-cyano-7-(3-(pyrrolidin-1-yl)propoxy)quinoline (100 mg), (prepared as described for the starting material in Example 11), was reacted with 5-amino-2-methylindole (51 mg) to give 6-cyano-4-(2-methylindol-5-ylamino)-7-(3-(pyrrolidin-1-yl)propoxy)quinoline hydrochloride (58 mg, 37%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-6123b285a0884ec98d785f1b4a7597a4
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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