3-Amino-1-propanol → HCID 25119827, compound

HRID 1893491Notes

Reaction equation

HRID 1893491 reaction equation
[CH2:1]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[C:14](Cl)[C:15]3[N:16]2[CH:19]=[CH:20][N:21]=3)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([CH2:30][OH:31])[CH2:28][NH2:29].C(N(C(C)C)CC)(C)C>O1CCOCC1>[CH2:1]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[C:14]([NH:29][CH2:28][CH2:27][CH2:30][OH:31])[C:15]3[N:16]2[CH:19]=[CH:20][N:21]=3)=[CH:11][C:10]=1[C:23]([F:26])([F:25])[F:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 59333340HCID 59333340, compound

Product 1

HCID 25119827HCID 25119827, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-benzyl-4-chloro-7-(trifluoromethyl)imidazo[1,2-a]quinoxalin-8-amine (30 mg; 0.079 mmol; 1 eq), 3-propanolamine (20 μl; 0.264 mmol; 3.3 eq) and diisopropylethylamine (15 μl; 0.088 mmol; 1.1 eq) in anhydrous 1,4-dioxane (0.5 ml) is stirred under argon at 100° C. for 16 h. Partition (ethyl acetate/aqueous ammonium chloride), washings of the organic phase (twice with aqueous ammonium chloride, once with brine), drying (magnesium sulfate) and concentration affords the title product (28 mg; 0.067 mmol; 86%) as a white solid.

Workup

  1. customPartition (ethyl acetate/aqueous ammonium chloride), washings of the organic phase (twice with aqueous ammonium chloride
  2. dry with materialonce with brine), drying
  3. concentration(magnesium sulfate) and concentration

Sources & evidence

ORD record
ord-7452b7bbfcb1481daec20d0dbac7f5f9
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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