2-Pyridineethanamine → HCID 11414891, compound

HRID 339409Notes

Reaction equation

HRID 339409 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH2:9].[N:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[C:11]=[O:12]>>[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:10][C:11]([NH:9][CH2:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:12])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 759192-PyridineethanamineHCID 94416p-Isopropylphenyl isocyanate

Product 1

HCID 11414891HCID 11414891, compoundYield 50%

Procedure

Prepared in a similar manner to example 158 using 2-(pyridine-2-yl)ethanamine and 1-isocyanato-4-isopropylbenzene. Purified via column chromatography (1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2) to afford 1-(4-isopropylphenyl)-3-(2-(pyridine-2-yl)ethyl)urea (130 mg, 50%) as a white solid. mp: 72-73° C. 1H NMR (500 MHz, CDCl3): δ 1.25 (d, 6H), 2.89 (m, 1H), 3.06 (t, 2H), 3.70 (t, 2H), 5.80 (br s, 1H), 6.55 (br s, 1H), 7.19 (m, 5H), 7.24 (d, 1H), 7.68 (dt, 1H), 8.46 (d, 1H). MS (M+H, 284).

Workup

  1. customPurified via column chromatography (1% MeOH in CH2Cl2 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-2b8672bc774e4e48858057d9fbf109be
Source dataset
uspto-grants-2014_11
Patent number
US08895050B2

Reaction notes

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