Hydrochloric Acid → HCID 117600382, compound

HRID 1746450Notes

Reaction equation

[Li]CCCC.[CH3:6][C:7]1[S:11][CH:10]=[N:9][CH:8]=1.[CH2:12]([O:19][C:20]1[N:25]=[C:24]([C:26](OC)=[O:27])[CH:23]=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1COCC1>[CH2:12]([O:19][C:20]1[N:25]=[C:24]([C:26]([C:10]2[S:11][C:7]([CH3:6])=[CH:8][N:9]=2)=[O:27])[CH:23]=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-BuLi (2.5 M in hexane, 16 mL, 40 mmol) in dry THF (120 mL) at −78° C. was added 5-methylthiazole (4.17 g, 40 mmol) drop wise over 20 minutes under nitrogen atmosphere. The mixture was stirred at −78° C. for 2 hrs and a solution of methyl 6-(benzyloxy)picolinate (4.7 g, 20 mmol) in THF (30 mL) was added drop wise over 20 minutes. After being stirred at −78° C. for 1 hr, the mixture was acidified with HCl (1N) to pH around 6 and extracted with ethyl acetate. The organic layer was concentrated and then diluted with MTBE. The white precipitate was collected by filtration to give A030-4. The remaining filtrate was concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (10/1) to afford A030-4. Total 6.2 g of (6-(benzyloxy)pyridin-2-yl)(5-methylthiazol-2-yl)methanone (85% yield) was obtained as a white solid.

Workup

stirringAfter being stirred at −78° C. for 1 hr
extractionextracted with ethyl acetate
concentrationThe organic layer was concentrated
additiondiluted with MTBE
filtrationThe white precipitate was collected by filtration
customto give A030-4
concentrationThe remaining filtrate was concentrated
customThe residue was purified by silica gel chromatography
washeluting with petroleum ether/ethyl acetate (10/1)
customto afford A030-4

Sources & evidence

ORD record: ord-c5c3fa1ca75d477381ee0545044d0da5
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150526B2

Reaction notes

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