Diisopropylethylamine → 4-Methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetra-hydro-pyran-4-yl)-amide

HRID 1923508Notes

Reaction equation

HRID 1923508 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:10][CH2:11][C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[N:14][O:15][CH:16]=2)[S:5][C:6]=1[C:7]([OH:9])=O.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.[NH2:54][CH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>CN(C=O)C>[O:58]1[CH2:59][CH2:60][CH:55]([NH:54][C:7]([C:6]2[S:5][C:4]([CH2:10][CH2:11][C:12]3[C:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)=[N:14][O:15][CH:16]=3)=[N:3][C:2]=2[CH3:1])=[O:9])[CH2:56][CH2:57]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666437194-Methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid

Product 1

HCID 497827144-Methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (tetra-hydro-pyran-4-yl)-amideYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-2-[2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (70 mg, 0.22 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (79 mg, 0.24 mmol), N,N-diisopropyl ethyl amine (190 μL, 1.11 mmol) and 4-aminotetrahydropyran (25 mg, 0.24 mmol). The resulting reaction mixture was stirred overnight and then evaporated. Purification by chromatography (silica, heptane:ethyl acetate 8:2 to 1:1) afforded the title compound (84 mg, 95%) as a white solid. S: m/e=399.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customevaporated
  3. customPurification by chromatography (silica, heptane:ethyl acetate 8:2 to 1:1)

Sources & evidence

ORD record
ord-285c5f0c39e24986a5ddb445b330f882
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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