Hydrochloric Acid → [3-(2-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]acetaldehyde

HRID 1942651Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[C:19](/[CH:24]=[CH:25]/[O:26]C)[C:18]=3[O:28][CH3:29])=[CH:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[S:13][C:14]([C:17]3[C:18]([O:28][CH3:29])=[C:19]([CH2:24][CH:25]=[O:26])[CH:20]=[C:21]([F:23])[CH:22]=3)=[CH:15][N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-5-{5-fluoro-2-(methyloxy)-3-[(E)-2-(methyloxy)ethenyl]phenyl}-1,3-thiazole (D79) (100 mg) in tetrahydrofuran (THF) (20 mL) under nitrogen was added HCl (0.5 mL). The reaction was heated to 70° C. for 2 h. The mixture was filtered and the filtrate was concentrated to give the crude product [3-(2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-5-fluoro-2-(methyloxy)phenyl]acetaldehyde (D80) (90 mg) as a brown oil. MS (ES): C21H19ClFNO3S requires 419. found 420.1 (M+H+).

Workup

filtrationThe mixture was filtered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-cb9e952ad38b4ce4a82fa1b0a9763c73
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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