2-Amino-2-methyl-1-propanol → HCID 46928970, compound

HRID 1514715Notes

Reaction equation

HRID 1514715 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.[NH2:59][C:60]([CH3:64])([CH3:63])[CH2:61][OH:62]>C1COCC1.CO.ClCCl>[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:59][C:60]([CH3:64])([CH3:63])[CH2:61][OH:62])=[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 118072-Amino-2-methyl-1-propanolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66718168HCID 66718168, compound

Product 1

HCID 46928970HCID 46928970, compoundYield 50.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (200 mg, 0.58 mmol) in THF (6 mL) were added 1-hydroxybenzotriazole hydrate (86.3 mg, 0.55 mmol), N-ethyldiisopropylamine (241 μL, 1.38 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (108 mg, 0.55 mmol) and 2-amino-2-methyl-1-propanol (50.7 mg, 0.55 mmol). The reaction mixture was stirred overnight at room temperature. Chromatography (silica, dichloromethane:methanol=0:100 to 95:5) afforded the title compound (120 mg, 50%) as a colourless oil. MS: m/e=434.4 [M+H]+.

Sources & evidence

ORD record
ord-61edff654bb14a2baec0122302ef9e18
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

Loading…