Hydrochloric Acid → HCID 67314388, compound

HRID 1011377Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C([O:24][C:25]([CH:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][C:36]2[N:41]=[C:40]3[CH2:42][O:43][C:44](=O)[C:39]3=[CH:38][CH:37]=2)[CH2:29][CH2:28]1)=[O:26])C.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:44]1[C:39]2[C:40](=[N:41][C:36]([CH2:35][CH2:34][CH2:33][N:30]3[CH2:29][CH2:28][CH:27]([C:25]([OH:26])=[O:24])[CH2:32][CH2:31]3)=[CH:37][CH:38]=2)[CH2:42][O:43]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 5-fluoro-1,3-dihydro-indol-2-one (150 mg, 1.0 mmol) in THF (5 mL) at room temperature is treated with lithium bis(trimethylsilyl)amide (1.0 M solution in tetrahydrofuran, 2.0 mL, 2.0 mmol) and stirred for 10 min. A solution of 1-[3-(5-oxo-5,7-dihydro-furo[3,4-b]pyridin-2-yl)-propyl]-piperidine-4-carboxylic acid ethyl ester (110 mg, 1 equiv) in anhydrous THF (2 mL) is added. The reaction mixture is stirred at room temperature for 3 h. The reaction mixture is poured into aqueous 2N HCl solution (10 mL) with stirring. Then it is heated at 60° C. for 2 h. To the mixture is then added ice water (100 mL) followed by the careful addition of saturated aqueous NaHCO3 to adjust the pH to 8. The foamy suspension is filtered and a greenish yellow solid is obtained. This material is purified by column chromatography to give the title compound as a yellow solid (48 mg, 33%).

Workup

stirringThe reaction mixture is stirred at room temperature for 3 h
stirringwith stirring
filtrationThe foamy suspension is filtered
customa greenish yellow solid is obtained
customThis material is purified by column chromatography

Sources & evidence

ORD record: ord-3590688a6d974c84bd77c2ad70bcc208
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977351B2

Reaction notes

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