Ethyl 4-amino-1-piperidinecarboxylate → HCID 24740405, compound

HRID 1990872Notes

Reaction equation

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

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 2-methylsulfanyl-benzooxazole-5-sulfonic acid amide (5.00 g, 20.5 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (3.53 g, 20.5 mmol, 1.0 equiv) in anhydrous acetonitrile (25 mL) was heated to 190° C. under microwave irradiation for 1 h. The crude reaction mixture was concentrated by evaporation under reduced pressure, the organic phase filtered over silica with ethyl acetate and purified by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water to afford 1.72 g (23%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.19 (t, J=7.1 Hz, 3H), 1.37-1.49 (m, 2H), 1.94-1.99 (m, 2H), 2.94-3.02 (m, 2H), 3.80-3.83 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.26 (br s, 2H), 7.49 (d, J=0.9 Hz, 2H), 7.63 (d, J=0.8 Hz, 1H), 8.28 (d, J=7.6 Hz, 1H). 13C NMR (75 MHz, DMSO): δ 14.56, 31.10, 42.05, 49.60, 60.65, 108.39, 112.71, 118.35, 140.08, 143.52, 149.76, 154.59, 162.67. MS (ISP): 368.9 [M+H]+.

Workup

customThe crude reaction mixture
concentrationwas concentrated by evaporation under reduced pressure
filtrationthe organic phase filtered over silica with ethyl acetate
custompurified by preparative HPLC on reversed phase
washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record: ord-5ddb29748f5045d98d10bde759a59c04
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Reaction notes

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