1H-1,2,4-Triazole → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-1,2-benzoxazole-5-carbaldehyde

HRID 245536Notes

Reaction equation

Cl[C:2]1[C:6]2[CH:7]=[C:8]([CH:20]=[O:21])[C:9]([N:12]3[CH2:17][C@H:16]([CH3:18])[O:15][C@H:14]([CH3:19])[CH2:13]3)=[C:10]([F:11])[C:5]=2[O:4][N:3]=1.C1CCN2C(=NCCC2)CC1.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1>C(#N)C>[CH3:19][C@H:14]1[O:15][C@@H:16]([CH3:18])[CH2:17][N:12]([C:9]2[C:8]([CH:20]=[O:21])=[CH:7][C:6]3[C:2]([N:33]4[CH:37]=[N:36][CH:35]=[N:34]4)=[N:3][O:4][C:5]=3[C:10]=2[F:11])[CH2:13]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde (Intermediate 534, 0.2 g, 0.68 mmol) in acetonitrile was added DBU (0.19 mL, 1.28 mmol) followed by 1,2,4-triazole (0.053 g, 0.76 mmol), and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was concentrated, the residue was purified by silica gel column chromatography using EtOAc in pet. ether to give title product.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1af048b5836c4053b13169d9e4274596
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658641B2

Reaction notes

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