Tetrahydrofuran → HCID 68522829, compound

HRID 2247720Notes

Reaction equation

HRID 2247720 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[C:12]([CH2:19][CH3:20])[CH:11]=1)(C(C)(C)C)(C)C.[F:21][C:22]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:23]=1[O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=O)=[CH:27][CH:26]=1.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[F:21][C:22]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:23]=1[O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]2[O:18][N:17]=[C:15]([C:13]3[S:14][C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[CH2:19][CH3:20])[N:16]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 2724141Tetrabutylammonium FluorideHCID 63037963HCID 63037963, compoundHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Product 1

HCID 68522829HCID 68522829, compound

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10f) using 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), 4-(2,3-difluorophenoxy)benzoic acid (0.14 g, 0.55 mmol) that was obtained in Example 18 (18a), N,N′-dicyclohexylcarbodiimide (0.11 g, 0.55 mmol), and 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.75 mL, 0.75 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 (2:8 to 3:7) as the eluent to afford the title compound (0.18 g) in a yield of 88% as a white crystalline solid.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-8d71c32711334cd7ab03db0f2a7b5009
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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