Morpholine → HCID 67455665, compound

HRID 469741Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([C:11]1[O:15][N:14]=[C:13]([NH:16][C:17]([C@@H:19]2[CH2:23][C@@H:22]([OH:24])[CH2:21][N:20]2[C:25]2[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=2)=[O:18])[CH:12]=1)([CH3:10])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C>O>[C:7]([C:11]1[O:15][N:14]=[C:13]([NH:16][C:17]([C@@H:19]2[CH2:23][C@@H:22]([OH:24])[CH2:21][N:20]2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:26]=2)=[O:18])[CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

Morpholine (0.01 mL, 0.115 mmol) is added to a solution of (2S,4R)-1-(2-chloro-pyrimidin-4-yl)-4-hydroxy-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (42 mg, 0.115 mmol) and diisopropylethylamine (0.02 mL, 0.115 mol). The reaction is stirred at 60° C. overnight. More morpholine (0.01 mL, 0.115 mmol) is added and the reaction is stirred at 80° C. for 3.5 hours. The reaction is diluted with water and extracted with ethyl acetate twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with methanol/dichloromethane provides the title compound. ESI m/z 417 [M+H+].

Workup

stirringthe reaction is stirred at 80° C. for 3.5 hours
extractionextracted with ethyl acetate twice
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by chromatography on silica eluting with methanol/dichloromethane

Sources & evidence

ORD record: ord-42bb6907347d4b36be4c6f3919ce72d5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Reaction notes

Loading…