3-[5-Allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide → HCID 59402797, compound

HRID 415586Notes

Reaction equation

[CH2:1]([C:4]1[S:8][C:7]([CH2:9][O:10][C:11]2[C:12]([F:21])=[C:13]([C:17]([F:20])=[CH:18][CH:19]=2)[C:14]([NH2:16])=[O:15])=[N:6][C:5]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:2]=[CH2:3]>CO>[F:21][C:12]1[C:11]([O:10][CH2:9][C:7]2[S:8][C:4]([CH2:1][CH2:2][CH3:3])=[C:5]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:6]=2)=[CH:19][CH:18]=[C:17]([F:20])[C:13]=1[C:14]([NH2:16])=[O:15]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-[5-allyl-4-(4-methoxy-phenyl)-thiazol-2-ylmethoxy]-2,6-difluoro-benzamide (0.1 g, 0.02 mmol) in 5 ml of anhydrous methanol was added dry 50 mg of dry Pd—C. The reaction mixture was stirred at 25° C. for 12 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400μ) using ethyl acetate/hexane (50:50) as the eluent to provide the title compound as white solid (0.02 g, 2%). 1H NMR (DMSO-d6, 400 MHz); δ 0.92 (t, 3H, J=7.2 Hz), 1.63-1.65 (m, 2H), 2.8 (t, 2H, J=7.6 Hz (o-coupling), 3.79 (s, 3H), 5.47 (s, 2H), 7.02 (d, 2H, J=8.8 Hz (o-coupling), 7.11 (m, 1H), 7.42 (m, 1H), 7.53 (d, 2H, J=8.8 Hz (o-coupling), 7.88 (s, 1H), 8.16 (s, 1H), 8.38 (d, 1H, J=8.4 Hz (o-coupling). MS ES+ (419.14), HPLC (method 5) Rt=16.58

Workup

dry with materialdry 50 mg of dry Pd—C
filtrationThe reaction mixture was filtered over the bed of celite
customThe filtrate was evaporated to dryness under reduced pressure
customthe residue was purified by column chromatography on silica (230-400μ)

Sources & evidence

ORD record: ord-e356476665af4fc3944441fc6fb2b51e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088791B2

Reaction notes

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