2-Aminopropanol → Rac-4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide

HRID 1923491Notes

Reaction equation

HRID 1923491 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[S:5][C:6]=1[C:7](O)=[O:8].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:55][CH:56]([CH3:59])[CH2:57][OH:58]>CN(C=O)C>[OH:58][CH2:57][CH:56]([NH:55][C:7]([C:6]1[S:5][C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:3][C:2]=1[CH3:1])=[O:8])[CH3:59]

Participants

6

Reactant 4

HCID 51262-AminopropanolHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66643564HCID 66643564, compound

Product 1

HCID 59568489Rac-4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amideYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (100 mg, 0.31 mmol) in DMF (3 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (108 mg, 0.33 mmol), N,N-diisopropyl ethyl amine (197 μL, 1.67 mmol) and rac-2-amino-1-propanol (30 mg, 0.40 mmol). The resulting reaction mixture was stirred for 2 h. The reaction mixture was extracted with ethyl acetate. The combined organic layers were then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, 0 to 2.5% methanol in dichlormethane) afforded the title compound (59 mg, 50%) as a colourless oil. MS: m/e=386.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were then dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. concentrationConcentration and purification by chromatography (silica, 0 to 2.5% methanol in dichlormethane)

Sources & evidence

ORD record
ord-844d4cab345646e483cb02d32ce93d81
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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