Methanol → HCID 135870805, compound

HRID 2233596Notes

Reaction equation

C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[S:15][C:16]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[NH:29][C:28](=[O:30])[O:27][N:26]=2)=[C:21]([Cl:31])[CH:20]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>ClCCl>[Cl:31][C:21]1[CH:20]=[C:19]([O:18][CH2:17][C:16]2[S:15][C:14]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:40])([F:41])[F:39])=[CH:34][CH:33]=3)=[N:13][C:12]=2[CH2:11][CH2:10][CH2:9][OH:8])[CH:24]=[CH:23][C:22]=1[C:25]1[NH:29][C:28](=[O:30])[O:27][N:26]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of 200 mg of 3-{4-[4-(3-benzyloxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-4H-[1,2,4]oxadiazol-5-one in 6 ml of dichloromethane cooled to −70° C. was added 0.8 mL of a 1 M solution of boron tribromide in dichloromethane. After stirring for 45 minutes at −60° C., the solution was poured into a mixture of methanol and a saturated aqueous solution of sodium hydrogenocarbonate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10) then crystallized from dichloromethane/diisopropylether to give 18 mg of 3-{2-chloro-4-[4-(3-hydroxy-propyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Workup

filtrationa saturated aqueous solution of sodium hydrogenocarbonate, filtered
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 90/10)
customthen crystallized from dichloromethane/diisopropylether

Sources & evidence

ORD record: ord-86b34dee67a740c7be062874c8008ad8
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

Loading…