3-Amino-1-propanol → HCID 57526905, compound

HRID 2261024Notes

Reaction equation

HRID 2261024 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13](S(C)=O)[N:12]=2)[N:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:7]1=[O:27])#[N:2].[NH2:32][CH2:33][CH2:34][CH2:35][OH:36]>O1CCOCC1>[C:1]([C:3]1[CH:31]=[CH:30][CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:32][CH2:33][CH2:34][CH2:35][OH:36])[N:12]=2)[N:8]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:7]1=[O:27])#[N:2]

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 23020390HCID 23020390, compound

Product 1

HCID 57526905HCID 57526905, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 70 mg of 1-(2-cyanobenzyl)-3-(4-fluorophenyl)-4-(2-methylsulfinylpyrimidin-4-yl)-4-imidazolin-2-one (Compound of Reference example 6(2) or Reference example 7(2)), 60.6 mg of 3-aminopropanol and 2 ml of dioxane was stirred at 80° C. for 5 hours. The reaction mixture was concentrated and then purified by silica gel column chromatography (chloroform:methanol=19:1) and crystallized from ether to give 44.6 mg of the title compound. Melting point: 166-167° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography (chloroform:methanol=19:1)
  3. customcrystallized from ether

Sources & evidence

ORD record
ord-0f08fb4262b840f1b9a376e386caa441
Source dataset
uspto-grants-2010_12
Patent number
US07846933B2

Reaction notes

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