Diisopropylethylamine → HCID 49783124, compound

HRID 1923501Notes

Reaction equation

HRID 1923501 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][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[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.[NH2:55][CH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[O:59]1[CH2:60][CH2:61][CH:56]([NH:55][C:7]([C:6]2[S:5][C:4]([CH2:10][CH2:11][C:12]3[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[N:14][O:15][C:16]=3[CH3:17])=[N:3][C:2]=2[CH3:1])=[O:9])[CH2:57][CH2:58]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66643567HCID 66643567, compound

Product 1

HCID 49783124HCID 49783124, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-2-[2-(5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (80 mg, 0.24 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (86 mg, 0.27 mmol), N,N-diisopropyl ethyl amine (210 μL, 1.21 mmol) and 4-aminotetrahydropyran (27 mg, 0.27 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 (97 mg, 97%) as a white solid. MS: m/e=413.2 [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-01a67ddfcb8c4edcafa749f29f73bdc2
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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