Hydrochloric Acid → HCID 46929062, compound

HRID 1514719Notes

Reaction equation

HRID 1514719 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 1200842-Amino-1-butanol, (+)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66718168HCID 66718168, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 46929062HCID 46929062, compoundYield 61%

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, 0.29 mmol) and [S]-(+)-2-amino-1-butanol (32.3 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 (73 mg, 61%) as a brown solid. MS: m/e=434.4 [M+H]+.

Sources & evidence

ORD record
ord-839e215e8d9a4bd6b41bd65c9f703eb8
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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