(2R)-2-(Methoxymethyl)pyrrolidine → HCID 90383089, compound

HRID 874431Notes

Reaction equation

Br[C:2]1[N:27]=[C:5]2[CH2:6][CH:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]3[S:20][CH:21]=[C:22]([CH:24]([F:26])[F:25])[N:23]=3)=[O:12])[CH2:8][CH2:9][N:4]2[N:3]=1.[CH3:28][O:29][CH2:30][C@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1>C(OCC)(=O)C>[F:25][CH:24]([F:26])[C:22]1[N:23]=[C:19]([C:14]2[CH:15]=[N:16][N:17]([CH3:18])[C:13]=2[C:11]([NH:10][CH:7]2[CH2:8][CH2:9][N:4]3[N:3]=[C:2]([N:32]4[CH2:33][CH2:34][CH2:35][C@@H:31]4[CH2:30][O:29][CH3:28])[N:27]=[C:5]3[CH2:6]2)=[O:12])[S:20][CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

The N-(2-bromo-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-4-(4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxamide (20 mg) obtained in (Example 5.16) <Step 7> and (R)-2-(methoxymethyl)pyrrolidine (0.5 ml) were heated at 150° C. for 4 days. Thereafter, ethyl acetate (50 ml) and a saturated saline (20 ml) were added to the reaction solution, and an organic layer was then extracted. The obtained organic layer was dried over sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by preparative thin-layer chromatography (silica gel: eluent; ethyl acetate), so as to obtain the title compound (2.1 mg) in a yellow amorphous form.

Workup

extractionan organic layer was then extracted
dry with materialThe obtained organic layer was dried over sodium sulfate
distillationThe solvent was distilled away under reduced pressure
customthe obtained residue was then purified by preparative thin-layer chromatography (silica gel: eluent; ethyl acetate)

Sources & evidence

ORD record: ord-786d6a36443444448fdf117326375196
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980889B2

Reaction notes

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