Tetrahydrofuran → HCID 68525865, compound

HRID 2247728Notes

Reaction equation

HRID 2247728 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Si]([O:48][CH2:49][C:50]1[S:54][C:53]([C:55](=[N:57]O)[NH2:56])=[C:52]([CH2:59][CH3:60])[CH:51]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:59]([C:52]1[CH:51]=[C:50]([CH2:49][OH:48])[S:54][C:53]=1[C:55]1[N:57]=[C:5]([C:4]2[CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)=[C:2]([F:1])[CH:3]=2)[O:7][N:56]=1)[CH3:60]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 28605150HCID 28605150, compoundHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Product 1

HCID 68525865HCID 68525865, compound

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 12 (12a) using 3-fluoro-4-(3-fluorophenoxy)benzoic acid (0.13 g, 0.53 mmol) that was obtained in Example 20 (20a), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.55 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.16 g, 0.50 mmol) that was obtained in Example 10 (10d), and 1.0 M solution of tetrabutylammoniumfluoride in tetrahydrofuran (1.0 mL, 1.0 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3) as the eluent to afford the title compound (0.18 g) in a yield of 87% as a pale yellow crystalline solid.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-fc4d09ec301841fe9b2ce149b1540e9b
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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