Benzyl Alcohol → 3-Amino-6-benzyloxy-5-chloro-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656665Notes

Reaction equation

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:19]1([NH:22][C:23]([C:25]2[S:38][C:28]3=[N:29][C:30](S(C)=O)=[C:31]([Cl:34])[C:32]([CH3:33])=[C:27]3[C:26]=2[NH2:39])=[O:24])[CH2:21][CH2:20]1>C1COCC1>[CH:19]1([NH:22][C:23]([C:25]2[S:38][C:28]3=[N:29][C:30]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[C:31]([Cl:34])[C:32]([CH3:33])=[C:27]3[C:26]=2[NH2:39])=[O:24])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of benzyl alcohol (0.541 g, 5.00 mmol) in THF (2.5 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes)(2.50 ml, 2.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 80° C. in a sealed tube for 2 hours, cooled to room temperature, and then quenched by the addition of water (15 ml). The mixture is diluted to 100 ml with water and then cooled to 0° C. and stirred. A yellow precipitate is formed. This solid is collected by filtration and purified by flash chromatography (1.5:1 hexane:EtOAc) to give the title compound as a pale yellow solid (0.130 g, 33%). Mass (m/z): 388.2 (M++1), 386.2 (M+−1).

Workup

temperaturecooled to room temperature
customquenched by the addition of water (15 ml)
additionThe mixture is diluted to 100 ml with water
temperaturecooled to 0° C.
stirringstirred
customA yellow precipitate is formed
filtrationThis solid is collected by filtration
custompurified by flash chromatography (1.5:1 hexane:EtOAc)

Sources & evidence

ORD record: ord-4dc36f73177840aea99b0f322128d872
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071776B2

Reaction notes

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