Isopropylamine → HCID 49782488, compound

HRID 1923511Notes

Reaction equation

HRID 1923511 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:3]=1[CH2:13][CH2:14][C:15]1[S:16][C:17]([C:20]([OH:22])=O)=[CH:18][N:19]=1.F[B-](F)(F)F.[N:28]1(OC(N(C)C)=[N+](C)C)[C:32]2[CH:33]=CC=C[C:31]=2N=N1.C(N(CC)C(C)C)(C)C.C(N)(C)C>CN(C=O)C>[CH:32]([NH:28][C:20]([C:17]1[S:16][C:15]([CH2:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:19][CH:18]=1)=[O:22])([CH3:33])[CH3:31]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66643592HCID 66643592, compound

Product 1

HCID 49782488HCID 49782488, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (77 mg, 0.24 mmol) in DMF (3 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (86 mg, 0.27 mmol), N,N-diisopropyl ethyl amine (208 μL, 1.21 mmol) and isopropylamine (16 mg, 0.27 mmol). The resulting reaction mixture was stirred for 2 h and then evaporated. Purification by chromatography (silica, heptane:ethyl acetate 1:1 to 0:1) afforded the title compound (81 mg, 93%) as an off white solid. MS: m/e=357.2 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customevaporated
  3. customPurification by chromatography (silica, heptane:ethyl acetate 1:1 to 0:1)

Sources & evidence

ORD record
ord-ffcdad0dbed24c8098799003d78eaf96
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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