tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-Butyl 4-(5-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylate

HRID 252875Notes

Reaction equation

HRID 252875 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16]([C:18]1[S:22][C:21]([C:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]=2)=[CH:20][CH:19]=1)=[O:17])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][C:5]=1[NH:15][C:16]([C:18]1[S:22][C:21]([CH:23]2[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]2)=[CH:20][CH:19]=1)=[O:17]

Participants

4

Reactant 1

HCID 59736975tert-Butyl 4-(5-(2-nitro-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59736744tert-Butyl 4-(5-(2-amino-5-(thiophen-2-yl)phenylcarbamoyl)thiophen-2-yl)piperidine-1-carboxylateYield 10%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 354 (270 mg, 0.53 mmol) in methanol (25 mL) was added 10% palladium on charcoal (150 mg). The resulting mixture was purged with H2 gas and stirred under a hydrogen atmosphere for 3 days, filtered through a celite pad, evaporated and purified by flash chromatography, eluent 1:1 hexanes-ethyl acetate, to afford the title compound 355 as a white solid (24 mg, 10% yield). 1H NMR: (CD3OD) δ 7.73 (d, J=3.3 Hz, 1H), 7.45 (d, J=2.1 Hz, 1H), 7.34 (dd, J=8.2, 2.2 Hz, 1H), 7.23-7.19 (m, 2H), 7.01 (dd, J=4.7, 3.7 Hz, 1H), 6.96 (d, J=3.9 Hz, 1H), 6.88 (d, J=8.1 Hz, 1H), 4.17 (d, J=13.1 Hz, 2H), 3.00-2.90 (m, 2H), 2.04 (d, J=12.1 Hz, 2H), 1.60-1.54 (m, 2H).

Workup

  1. customThe resulting mixture was purged with H2 gas
  2. filtrationfiltered through a celite pad
  3. customevaporated
  4. custompurified by flash chromatography, eluent 1:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-277907a43b6b4c66a2c872213ec4b027
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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