Cyclobutylamine → HCID 46929238, compound

HRID 1514743Notes

Reaction equation

HRID 1514743 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][N:13]=2)=[C:8]([CH2:21][OH:22])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH:23]1([NH2:27])[CH2:26][CH2:25][CH2:24]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:27][CH:23]3[CH2:26][CH2:25][CH2:24]3)=[O:18])=[CH:14][N:13]=2)=[C:8]([CH2:21][OH:22])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66718228HCID 66718228, compound

Product 1

HCID 46929238HCID 46929238, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-[3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (49 mg, 0.16 mmol) in DMF (2 mL) was added cyclobutylamine (25 mg, 0.35 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (82 mg, 0.26 mmol) and N-ethyldiisopropylamine (136 μL, 0.80 mmol) with DMF (1 mL). The reaction mixture was stirred for 17 h at room temperature. The reaction was partitioned between water and ethyl acetate. The aqueous phase was extracted two times with ethyl acetate and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude material was purified by chromatography (silica, dichloromethane:methanol 100:0 to 97:3) to afford the title compound (36 mg, 63%) as a colorless gum. MS: m/e=360.3 [M+H]+.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted two times with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a yellow oil
  6. customThe crude material was purified by chromatography (silica, dichloromethane:methanol 100:0 to 97:3)

Sources & evidence

ORD record
ord-d37ab70a64bb462bafaa4185333bd533
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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