4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole → HCID 57941447, compound

HRID 1438089Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.Cl[CH2:17][C:18]1[N:19]=[C:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[S:21][CH:22]=1>CN(C)C=O>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[S:21][CH:22]=[C:18]([CH2:17][N:3]3[C:4](=[O:15])[C:5]4[C@@H:6]5[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]5)[C:10]=4[N:2]3[CH3:1])[N:19]=2)=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 100 mg, 0.49 mmol) and 4-chloromethyl-2-(4-chlorophenyl)-thiazole (Maybridge plc, Tintagel, Cornwall, UK; 153 mg, 0.63 mmol) in dimethylformamide (5 mL) was heated at 100° C. for 2 days. The solvent was evaporated and ethyl acetate (50 mL) was added. The solution was washed with water (twice) and brine, dried (magnesium sulfate), filtered, evaporated and purified by chromatography, eluting with 2-3% methanol/dichloromethane to give (4S,7R)-2-[2-(4-Chloro-phenyl)-thiazol-4-ylmethyl]-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (89 mg, 44%) as an off-white foam. APCI(+)-MS (M+H) 414.

Workup

customThe solvent was evaporated
additionethyl acetate (50 mL) was added
washThe solution was washed with water (twice) and brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
customevaporated
custompurified by chromatography
washeluting with 2-3% methanol/dichloromethane

Sources & evidence

ORD record: ord-787e3644be8b45879ad66666f66363ad
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

Loading…