Cyclopentylamine → HCID 11350436, compound

HRID 1925192Notes

Reaction equation

HRID 1925192 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14]([CH2:15][C:16]([O:18]CC)=O)[N:13]=[C:12]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14]([CH2:15][C:16]([NH:32][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:18])[N:13]=[C:12]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 86609774HCID 86609774, compound

Product 1

HCID 11350436HCID 11350436, compoundYield 75%

Procedure

A mixture of ethyl {5-[3-chloro-4-(methyloxy)phenyl]-3-pyridin-4-yl-1H-1,2,4-triazol-1-yl}acetate (0.2 mmol) and cyclopentylamine (4 mL) were heated to reflux for 2 h. The mixture was cooled to room temperature and the excess cyclopentylamine was removed in vacuo. The crude solid was then triturated with methanol to afford the pure product (0.061 g, 75%). 1H NMR (400 MHz, d6-DMSO): δ 8.68 (dd, 2H), 7.92 (22, 2H), 7.82 (m, 1H), 7.75 (dd, 1H), 7.33 (d, 1H), 4.95 (s, 2H), 4.00 (m, 1H), 3.94 (s, 3H), 1.80 (m, 2H), 1.64 (m, 2H), 1.51 (m, 2H), 1.40 (m, 2H). MS (EI) for C21H23ClN5O2: 412 (MH+).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 2 h
  3. customthe excess cyclopentylamine was removed in vacuo
  4. customThe crude solid was then triturated with methanol

Sources & evidence

ORD record
ord-999e39212c2f40449ad80712797f839b
Source dataset
uspto-grants-2012_05
Patent number
US08178570B2

Reaction notes

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