3-(5-Allyl-thiazolo[5,4-b]pyridin-2-ylmethoxy)-2,6-difluoro-benzamide → 2,6-Difluoro-3-(5-propyl-thiazolo[5,4-b]pyridin-2-ylmethoxy)-benzamide

HRID 538578Notes

Reaction equation

[CH2:1]([C:4]1[N:9]=[C:8]2[S:10][C:11]([CH2:13][O:14][C:15]3[C:16]([F:25])=[C:17]([C:21]([F:24])=[CH:22][CH:23]=3)[C:18]([NH2:20])=[O:19])=[N:12][C:7]2=[CH:6][CH:5]=1)[CH:2]=[CH2:3]>CO.[Pd]>[F:25][C:16]1[C:15]([O:14][CH2:13][C:11]2[S:10][C:8]3[C:7]([N:12]=2)=[CH:6][CH:5]=[C:4]([CH2:1][CH2:2][CH3:3])[N:9]=3)=[CH:23][CH:22]=[C:21]([F:24])[C:17]=1[C:18]([NH2:20])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(5-Allyl-thiazolo[5,4-b]pyridin-2-ylmethoxy)-2,6-difluoro-benzamide (0.018 g, 0.049 mmol) in 5 ml of anhydrous methanol was added Pd—C (10%, 5 mg) and the reaction mixture was stirred at 25° C. for 12 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite and the filtrate was evaporated to dryness under reduced pressure to give the title compound as white solid (0.0078 g, 43%). 1H NMR (DMSO-d6, 400 MHz); δ 0.91 (m, 3H), 1.65 (m, 2H), 2.74 (m, 2H), 5.69 (s, 2H), 7.12 (m, 1H), 7.39 (m, 1H), 7.90 (br s, 1H), 8.18 (br s, 1H), 8.27 (br s, 1H) and 8.52 (br s, 1H). MS ES+(364.11), HPLC (method I) Rt=15.85 min.

Workup

filtrationThe reaction mixture was filtered over the bed of celite
customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-a98cbb34974749278edcc71b641ebc6a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865736B2

Reaction notes

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