2-Morpholinoethanol → HCID 11575133, compound

HRID 656643Notes

Reaction equation

HRID 656643 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:20]1([NH:23][C:24]([C:26]2[S:39][C:29]3=[N:30][C:31](S(C)=O)=[C:32]([Cl:35])[C:33]([CH3:34])=[C:28]3[C:27]=2[NH2:40])=[O:25])[CH2:22][CH2:21]1>C1COCC1.O>[CH:20]1([NH:23][C:24]([C:26]2[S:39][C:29]3=[N:30][C:31]([O:1][CH2:2][CH2:3][N:4]4[CH2:9][CH2:8][O:7][CH2:6][CH2:5]4)=[C:32]([Cl:35])[C:33]([CH3:34])=[C:28]3[C:27]=2[NH2:40])=[O:25])[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 611632-MorpholinoethanolHCID 2733832Lithium HexamethyldisilazideHCID 576644203-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Product 1

HCID 11575133HCID 11575133, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2-hydroxyethyl)morpholine (5.72 g, 43.62 mmol) in THF (25 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)-amide (1.0 M in hexanes) (21.80 ml, 21.80 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 (30 g, 8.72 mmol). The reaction vessel is sealed and heated at 80° C. for 3 hours. The reaction is cooled to room temperature and quenched by the addition of water (200 ml). A yellow precipitate is formed. The mixture is diluted to 350 ml with water and cooled to 0° C. The yellow precipitate is collected by filtration. The solid is slurried in 100 ml of 3:1 hexane:EtOAc and stirred for 10 minutes. The mixture is filtered, and the collected solid is dried in the vacuum oven overnight to afford the title compound as a yellow solid (2.11 g, 59%). Mass (m/z): 411.1 (M++1), 409.1 (M+−1).

Workup

  1. customThe reaction vessel is sealed
  2. temperatureThe reaction is cooled to room temperature
  3. customquenched by the addition of water (200 ml)
  4. customA yellow precipitate is formed
  5. temperaturecooled to 0° C
  6. filtrationThe yellow precipitate is collected by filtration
  7. stirringEtOAc and stirred for 10 minutes
  8. filtrationThe mixture is filtered
  9. customthe collected solid is dried in the vacuum oven overnight

Sources & evidence

ORD record
ord-6628e1f4dfca46cd9a144db8126151c1
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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