Boron Trichloride → 1-(3-Hydroxy-propyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259397Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([C:25]2([CH2:28][CH2:29][CH2:30][O:31]CC3C=CC=CC=3)[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16].B(Cl)(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([NH:21][S:22]([C:25]2([CH2:28][CH2:29][CH2:30][OH:31])[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:12]2[O:20][CH2:19][CH2:18][N:13]2[C:14](=[O:17])[C:15]=1[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

1-(3-Benzyloxy-propyl)cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide (0.23 g, 0.352 mmol) in DCM (10 mL) was reacted with 1M BCl3 (0.12 g, 1.056 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 3 hours. Purification by column chromatography on silica gel (4% MeOH in CHCl3) afforded 70 mg of the product (36% yield).

Workup

customPurification by column chromatography on silica gel (4% MeOH in CHCl3)

Sources & evidence

ORD record: ord-63cb03b9a04d41e4b93db0b524780c22
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466289B2

Reaction notes

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