Cyanomethylenetributylphosphorane → HCID 118030927, compound

HRID 1777399Notes

Reaction equation

O[CH2:2][C@H:3]1[N:8]([C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=2[N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[O:10])[C@@H:7]([CH3:23])[CH2:6][CH2:5][O:4]1.C(C=P(CCCC)(CCCC)CCCC)#N.[F:40][C:41]1[CH:42]=[CH:43][C:44]([C:47]2[CH:48]=[N:49][NH:50][CH:51]=2)=[N:45][CH:46]=1>C1(C)C=CC=CC=1>[F:40][C:41]1[CH:42]=[CH:43][C:44]([C:47]2[CH:51]=[N:50][N:49]([CH2:2][C@H:3]3[N:8]([C:9]([C:11]4[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=4[N:18]4[N:19]=[CH:20][CH:21]=[N:22]4)=[O:10])[C@@H:7]([CH3:23])[CH2:6][CH2:5][O:4]3)[CH:48]=2)=[N:45][CH:46]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of [(2S,4S)-2-(hydroxymethyl)-4-methyl-1,3-oxazinan-3-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone obtained in Reference Example 17 (0.070 g, 0.22 mmol) in toluene (1 mL), 5-fluoro-2-(1H-pyrazol-4-yl)pyridine obtained in Reference Example 11 (0.040 g, 0.24 mmol) and cyanomethylene tributylphosphorane (0.087 mL, 0.33 mmol) were added, and the resulting mixture was stirred with heating for 3 hours at 100° C. The solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (KP-NH 12 g, hexane/EtOAc=80/20 to 0/100) (HP-Sil 10 g, hexane/EtOAc=80/20 to 0/100) to obtain the title compound (0.11 g) (colorless oil).

Workup

additionwere added
distillationThe solvent was distilled off under reduced pressure
customthe obtained residue was purified by column chromatography (KP-NH 12 g, hexane/EtOAc=80/20 to 0/100) (HP-Sil 10 g, hexane/EtOAc=80/20 to 0/100)

Sources & evidence

ORD record: ord-67d52c81ab7a4e5ea6e85ae649707a83
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266870B2

Reaction notes

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