Diisopropylethylamine → HCID 68521108, compound

HRID 2247646Notes

Reaction equation

HRID 2247646 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][CH:13]=[C:12]([C:15](=[N:17][OH:18])[NH2:16])[CH:11]=1)(C(C)(C)C)(C)C.[C:19]1([C:25]2[CH:26]=[C:27]([C:34](Cl)=O)[S:28][C:29]=2[C:30]([F:33])([F:32])[F:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:19]1([C:25]2[CH:26]=[C:27]([C:34]3[O:18][N:17]=[C:15]([C:12]4[CH:11]=[C:10]([CH2:9][OH:8])[S:14][CH:13]=4)[N:16]=3)[S:28][C:29]=2[C:30]([F:33])([F:31])[F:32])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 71711994-Phenyl-5-(trifluoromethyl)thiophene-2-carbonyl chlorideHCID 866202125-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxythiophene-3-carboximidamide

Product 1

HCID 68521108HCID 68521108, compound

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1e) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxythiophene-3-carboximidamide (0.43 g, 1.5 mmol) that was obtained in Example 3 (3b), 4-phenyl-5-(trifluoromethyl)thiophene-2-carbonyl chloride (0.52 g, 1.8 mmol), N,N-diisopropylethylamine (0.52 ml, 3.0 mmol), and a 1.0 M solution of tetrabutylammonium fluoride (3.0 ml, 3.0 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 (1:2 to 1:1) as the eluent to afford the title compound (0.60 g) as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-13f4817d35ee42078db6a61f48ff860b
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…