Methanol → HCID 178507372, compound

HRID 16684Notes

Reaction equation

HRID 16684 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([NH:20]C(=O)OC(C)(C)C)=[CH:16][CH:17]=3)[C:12]=2[NH:28][C:29]([C@H:31]2[CH2:36][CH2:35][C@H:34]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:33][CH2:32]2)=[O:30])=[O:10])=[N:6][CH:7]=1.Cl.O1CCOCC1.CO>O1CCOCC1>[NH2:20][C:15]1[N:14]=[C:13]2[C:12]([NH:28][C:29]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)[CH2:33][CH2:32]3)=[O:30])=[C:11]([C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])[O:19][C:18]2=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 178452646HCID 178452646, compound

Product 1

HCID 178507372HCID 178507372, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

t-Butyl (2-{[(5-chloropyridin-2-yl)amino]carbonyl}-3-{[(trans-4-pyrrolidin-1-ylcyclohexyl)carbonyl]amino}furo[3,2-b]pyridin-5-yl)carbamate (280 mg) obtained in Example 96 is suspended in dioxane (3 ml). To the suspension is added 4 N hydrogen chloride-dioxane solution (3 ml). The reaction solution is warmed to room temperature, and thereto is added methanol (2 ml), followed by stirring for 8 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is suspended in diethyl ether. The precipitates are collected by filtration to give the title compound (266 mg) as hydrochloride. The resulting hydrochloride is suspended in chloroform and thereto is added saturated aqueous sodium hydrogen carbonate solution. The precipitated solid is collected by filtration to give the title compound (88 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. filtrationThe precipitates are collected by filtration

Sources & evidence

ORD record
ord-fd517eb592184498bb60b9dda00f255e
Source dataset
uspto-grants-2010_06
Patent number
US07737161B2

Reaction notes

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