Piperidine → 7-Benzyloxy-2-phenyl-4-piperidin-1-yl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642380Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](I)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])[CH3:2].[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 7-benzyloxy-4-iodo-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (165 mg, 0.32 mmole), piperidine (95 μl, 0.96 mmole) and triethylamine (89 μl, 0.64 mmole) in ethanol (1.6 ml) was heated at 130° C. in a CEM microwave synthesizer for 30 min before it was cooled to room temperature, concentrated and purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a green oil (24 mg). MS: (+) m/z 474.55 (M+1).

Workup

temperaturewas cooled to room temperature
concentrationconcentrated
custompurified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Sources & evidence

ORD record: ord-4a58cb50d2374b09a12b42e9013e8e13
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696223B2

Reaction notes

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