HCID 58992678, compound → HCID 58992595, compound

HRID 602206Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]4[CH:24]=[CH:25][C:26]([N+:33]([O-])=O)=[C:27]([CH:32]=4)[C:28]([O:30][CH3:31])=[O:29])[CH2:18]3)=[O:15])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1>C(O)(=O)C>[NH2:33][C:26]1[CH:25]=[CH:24][C:23]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([NH:16][C:14]([C:10]3[S:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[N:12][C:11]=3[CH3:13])=[O:15])[CH2:18]2)=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 5-[3-[[2-(4-chlorophenyl)-4-methylthiazole-5-carbonyl]amino]piperidin-1-yl]-2-nitrobenzoate (14.6 g, 28.4 mmol) was suspended in acetic acid (140 mL). To this suspension, reduced iron (9.49 g, 170 mmol) was added and the mixture was stirred at 80° C. for 3 hours. The mixture was then allowed to cool and was filtered through Celite. The solvent was removed and a saturated aqueous sodium bicarbonate solution was added to the residue to make it basic. The crystallized powdery product was collected by filtration and washed with water. The resulting powder was dissolved in ethyl acetate and was filtered through Celite. The solvent was then removed to give 12.7 g (26.2 mmol, 92%) of the desired compound as a pale yellow powder.

Workup

temperatureto cool
filtrationwas filtered through Celite
customThe solvent was removed
additiona saturated aqueous sodium bicarbonate solution was added to the residue
filtrationThe crystallized powdery product was collected by filtration
washwashed with water
dissolutionThe resulting powder was dissolved in ethyl acetate
filtrationwas filtered through Celite
customThe solvent was then removed

Sources & evidence

ORD record: ord-d11b4df8fc384452a1859b952b4c449f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902367B2

Reaction notes

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