1,4-Dioxane hydrochloride → N-(azetidin-3-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine hydrochloride

HRID 526889Notes

Reaction equation

HRID 526889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]4)[C:14]([F:29])=[CH:13][N:12]=3)=[CH:9][N:8]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:5]2=[N:6][CH:7]=1.Cl.O1CCOCC1>CO>[ClH:1].[NH:20]1[CH2:19][CH:18]([NH:17][C:15]2[C:14]([F:29])=[CH:13][N:12]=[C:11]([C:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:8]([S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[CH:9]=3)[N:16]=2)[CH2:21]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67289632tert-butyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate2×

Product 1

HCID 67284924N-(azetidin-3-yl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of tert-butyl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate, 6b, (0.23 g, 0.40 mmol) in methanol (10 mL) was treated with 4N HCl/dioxane (5 mL, 20 mmol) then heated at 80° C. for 30 minutes.

Sources & evidence

ORD record
ord-f255f77754cc42e096c9ad8dc04e4285
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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