Piperidine → HCID 178465737, compound

HRID 598208Notes

Reaction equation

HRID 598208 reaction equation
[C:1]([CH2:3][C:4]([N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[O:5])#[N:2].[CH2:20]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH3:21].N1CCCCC1>C(O)C>[C:1]([C:3](=[CH:32][C:29]1[CH:28]=[CH:27][C:26]([S:23](=[O:25])(=[O:24])[NH:22][CH2:20][CH3:21])=[CH:31][CH:30]=1)[C:4]([N:6]([CH:17]([CH3:19])[CH3:18])[C:7]1[CH:16]=[CH:15][C:10]2[N:11]=[C:12]([SH:14])[S:13][C:9]=2[CH:8]=1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53650177N-Ethyl-4-formylbenzene-1-sulfonamideHCID 178457774HCID 178457774, compound

Product 1

HCID 178465737HCID 178465737, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

α-cyano-N-isopropyl-N-(2-mercaptobenzothiazol-6-yl)acetamide (71 mg, 0.244 mmol) and N-ethyl-4-formylbenzenesulfonamide (52 mg, 0.244 mmol) were combined in absolute ethanol (1 ml). The mixture was stirred 15 minutes with activated 4 A molecular sieves in a sealed vessel. Piperidine (27 μL, 0.268 mmol) was added and the mixture was heated to 80° C. After 1.5 hours, the solution was concentrated in vacuo and purified by preparative TLC (50% ethyl acetate, 50% hexanes) to yield 19 mg (16%). 1H NMR (CDCl3) δ=1.08 (t, 3H), 1.20 (m, 6H), 2.99 (t, 2H), 4.98 (m, 1H), 5.41 (m, 1H), 7.17 (d, 1H), 7.32 (m, 3H), 7.81 (d, 2H), 7.88 (d, 2H), 7.96 (s, 1H).

Workup

  1. waitAfter 1.5 hours
  2. concentrationthe solution was concentrated in vacuo
  3. custompurified by preparative TLC (50% ethyl acetate, 50% hexanes)
  4. customto yield 19 mg (16%)

Sources & evidence

ORD record
ord-3ba76ab73bc5465680b1cee0570bcc62
Source dataset
uspto-grants-2011_03
Patent number
US07897615B2

Reaction notes

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