Diisopropylethylamine → HCID 46929063, compound

HRID 1514720Notes

Reaction equation

HRID 1514720 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([CH2:14][O:15][C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=3)=[C:12]([CH2:25][OH:26])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC.[CH3:59][N:60]1[CH:64]=[C:63]([NH2:65])[CH:62]=[N:61]1>C1COCC1.CCCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([CH2:14][O:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH:65][C:63]4[CH:62]=[N:61][N:60]([CH3:59])[CH:64]=4)=[O:21])=[CH:18][N:17]=3)=[C:12]([CH2:25][OH:26])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 47709901-methyl-1H-pyrazol-4-amineHCID 66718168HCID 66718168, compound

Product 1

HCID 46929063HCID 46929063, compoundYield 3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (100 mg, 0.28 mmol) in THF (3 mL) were added 1-hydroxybenzotriazole hydrate (43.1 mg, 0.28 mmol), N-ethyldiisopropylamine (120 μL, 0.69 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (54.0 mg, 0.28 mmol) and 1-methyl-1H-pyrazol-4-ylamine (26.8 mg, 0.28 mmol). The reaction mixture was stirred overnight at room temperature. Chromatography (silica, ethyl acetate:heptane=2:1 to 9) afforded the title compound (3.5 mg, 3%) as a colourless oil. MS: m/e=442.2 [M+H]+.

Sources & evidence

ORD record
ord-90a052e403db40d7b8df4a5438ef0a2f
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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