1,3-Propanediol → 3-Amino-5-chloro-N-cyclopropyl-6-(3-hydroxypropoxy)-4-methylthieno[2,3-b]pyridine-2-carboxamide

HRID 656649Notes

Reaction equation

[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:16]1([NH:19][C:20]([C:22]2[S:35][C:25]3=[N:26][C:27](S(C)=O)=[C:28]([Cl:31])[C:29]([CH3:30])=[C:24]3[C:23]=2[NH2:36])=[O:21])[CH2:18][CH2:17]1>C1COCC1>[CH:16]1([NH:19][C:20]([C:22]2[S:35][C:25]3=[N:26][C:27]([O:4][CH2:3][CH2:2][CH2:1][OH:5])=[C:28]([Cl:31])[C:29]([CH3:30])=[C:24]3[C:23]=2[NH2:36])=[O:21])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1,3-propanediol (1.053 g, 13.84 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (3.50 ml, 3.50 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 75° C. for 1 hour, cooled to room temperature, and then quenched by the addition of water (15 ml). Ice is added to the reaction mixture and, while stirring, a yellow precipitate is formed. This solid is collected by filtration and placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.240 g, 67%). Mass (m/z): 356.2 (M++1), 354.1 (M+−1).

Workup

temperaturecooled to room temperature
customquenched by the addition of water (15 ml)
additionIce is added to the reaction mixture
stirringwhile stirring
customa yellow precipitate is formed
filtrationThis solid is collected by filtration
customto dry (60° C. for 16 hours)

Sources & evidence

ORD record: ord-d0d00d2d9e3e4dda843fee1e2db75652
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071776B2

Reaction notes

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