Diisopropylethylamine → HCID 46928865, compound

HRID 1514703Notes

Reaction equation

HRID 1514703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:26][CH:27]([NH2:32])[C:28]([F:31])([F:30])[F:29].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:32][C@@H:27]([CH3:26])[C:28]([F:31])([F:30])[F:29])=[O:21])=[CH:17][N:16]=3)=[C:11]([CH2:24][OH:25])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 37831651,1,1-Trifluoro-2-propanamineHCID 667181326-[3-(4-Chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 46928865HCID 46928865, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[3-(4-chloro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (100 mg, 0.28 mmol) and L-2,2,2-trifluoro-1-(methyl)ethylamine (32 mg, 0.28 mmol) in THF (10 mL) were added at 0° C., 1-hydroxybenzotriazole hydrate (43.3 mg, 0.28 mmol), N-ethyldiisopropylamine (121 μL, 0.69 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (54.2 mg, 0.28 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was removed by distillation. The remaining material was purified by chromatography (silica, ethyl acetate:heptane=2:8 to 1:0, then silica, dichloromethane:methanol=99:1 to 95:5) to afford the title compound (75 mg, 60%) as a white solid. MS: m/e=454.1 [M−H]−.

Workup

  1. customThe solvent was removed by distillation
  2. customThe remaining material was purified by chromatography (silica, ethyl acetate

Sources & evidence

ORD record
ord-1e207977743646af950a4201b51c91b7
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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