Hydrochloric Acid → HCID 46929061, compound

HRID 1514718Notes

Reaction equation

HRID 1514718 reaction equation
O.[OH:2][C:3]1[C:11]2[N:10]=NN[C:7]=2[CH:6]=CC=1.C(N(C(C)C)C(C)C)C.CCN=C=NCCCN(C)C.Cl.[F:33][C:34]1[CH:35]=[C:36]([C:41]2[C:45]([CH2:46][O:47][C:48]3[CH:56]=[CH:55][C:51]([C:52]([OH:54])=O)=[CH:50][N:49]=3)=[C:44]([CH2:57][OH:58])[O:43][N:42]=2)[CH:37]=[CH:38][C:39]=1[F:40].N[C@H](CC)CO.Cl>C1COCC1.CCCCCCC.C(OCC)(=O)C>[F:33][C:34]1[CH:35]=[C:36]([C:41]2[C:45]([CH2:46][O:47][C:48]3[CH:56]=[CH:55][C:51]([C:52]([NH:10][C@@H:11]([CH2:3][OH:2])[CH2:7][CH3:6])=[O:54])=[CH:50][N:49]=3)=[C:44]([CH2:57][OH:58])[O:43][N:42]=2)[CH:37]=[CH:38][C:39]=1[F:40]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27238562-Amino-1-butanol, (-)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66718168HCID 66718168, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 46929061HCID 46929061, compoundYield 38%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent

Procedure

Hydroxybenzotriazole hydrate (43.1 mg, 0.28 mmol), N-ethyldiisopropylamine (241 μL, 1.38 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (54.0 mg, 0.28 mmol) were added at 0° C. to a solution 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (100 mg, 0.28 mmol) and [R]-(−)-2-amino-1-butanol (32.4 μL, 0.33 mmol) in THF (8 mL). The reaction mixture was stirred at room temperature overnight. Addition of aqueous hydrochloric acid (1 N, 10 mL), extraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=0:1 to 1:0) afforded the title compound (45 mg, 38%) as a white solid. MS: m/e=434.4 [M+H]+.

Sources & evidence

ORD record
ord-f8ba9fae3b214c848f31c089d3326d04
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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