1H-Pyrrolo[2,3-b]pyridin-5-ol → 4-(7-azaindol-5-yloxy)-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline

HRID 916395Notes

Reaction equation

HRID 916395 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]([CH3:21])[CH2:18][C:19]#[CH:20])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:22][C:23]1[CH:24]=[C:25]2[C:29](=[N:30][CH:31]=1)[NH:28][CH:27]=[CH:26]2>>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([O:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][N:17]([CH3:21])[CH2:18][C:19]#[CH:20])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)=[CH:31][N:30]=2)[CH:26]=[CH:27]1

Participants

3

Reactant 2

HCID 220307221H-Pyrrolo[2,3-b]pyridin-5-olHCID 589602564-chloro-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline

Product 1

HCID 101508244-(7-azaindol-5-yloxy)-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazolineYield 47.3%

Procedure

Using an analogous procedure to that described for the preparation of Example 5, 4-chloro-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline (0.25 g, 0.817 mmol) was reacted with 5-hydroxy-7-azaindole (0.12 g, 0.899 mmol), (prepared as described for the starting material in Example 2), to give 4-(7-azaindol-5-yloxy)-6-methoxy-7-[2-(N-methyl-N-prop-2-yn-1-ylamino)ethoxy]quinazoline (0.156 g, 47%).

Workup

  1. custom(prepared

Sources & evidence

ORD record
ord-01c4ff47fea54ed7850376affa3e0bcc
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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