N-(2-Aminoethyl)piperidine → HCID 10194112, compound

HRID 2416203Notes

Reaction equation

HRID 2416203 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[C:14](=[O:23])[NH:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]=2)[CH:5]=[CH:4][N:3]=1.NCC[N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[N:27]1([C:2]2[CH:7]=[C:6]([C:8]3[S:9][CH:10]=[C:11]([C:13]4[C:14](=[O:23])[NH:15][C:16]5[C:21]([CH:22]=4)=[CH:20][CH:19]=[CH:18][CH:17]=5)[N:12]=3)[CH:5]=[CH:4][N:3]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 10308794HCID 10308794, compound

Product 1

HCID 10194112HCID 10194112, compound

Conditions

Temperature
128 °C

Procedure

A mixture of 3-[2-(2-chloro-pyridin-4-yl)-thiazol-4-yl]-1H-quinolin-2-one (Example 85, 60 mg, 0.18 mmol) and 1-(2-aminoethyl)piperidine (Aldrich-Sigma Company, 2 mL) was heated at 128° C. for 48 h. The reaction was quenched by addition of 10 mL of H2O. The precipitates were collected by filtration and purified by Gilson preparative HPLC to provide the title compound as a yellow solid after lyophilization. MS m/z: 389.3 (M+1). HRMS m/z: 389.1398 (M+H+, C22H20N4OS Calc'd 389.1431).

Workup

  1. customThe reaction was quenched by addition of 10 mL of H2O
  2. filtrationThe precipitates were collected by filtration
  3. custompurified by Gilson preparative HPLC

Sources & evidence

ORD record
ord-44c9470394f7459aa70d5e329cb5be7c
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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