Isopropylamine → HCID 49803874, compound

HRID 1962978Notes

Reaction equation

HRID 1962978 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([OH:23])=O)=[N:19][CH:20]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[N:6][CH:7]=1.F[B-](F)(F)F.[N:30]1(OC(N(C)C)=[N+](C)C)[C:34]2[CH:35]=CC=C[C:33]=2N=N1.C(N(CC)C(C)C)(C)C.C(N)(C)C>CN(C=O)C>[CH:34]([NH:30][C:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)=[N:9][O:10][C:11]=2[CH3:24])=[CH:20][N:19]=1)=[O:23])([CH3:35])[CH3:33]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66644519HCID 66644519, compound

Product 1

HCID 49803874HCID 49803874, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-pyridine-2-carboxylic acid (75 mg, 0.23 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (81 mg, 0.25 mmol), N,N-diisopropyl ethyl amine (195 μL, 1.14 mmol) and isopropylamine (22 μL, 0.25 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was evaporated and purification by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3) afforded the title compound (60 mg, 71%) as a white solid. MS: m/e=371.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was evaporated
  3. custompurification by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3)

Sources & evidence

ORD record
ord-c5e351116a45472aa1b184497dc90529
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

Loading…