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 415653Notes

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-7415ddf9d84b4db986dc116561dd3f79
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088791B2

Reaction notes

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