Disiloxane → 3-[5-(4-Chlorophenyl)pyridin-2-yl]propynoic acid-[4-(4-hydroxypiperidin-1-ylmethyl)phenyl]amide

HRID 735075

Reaction equation

HRID 735075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[Si]([O:26][CH:27]1[CH2:32][CH2:31][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)[CH2:29][CH2:28]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[SiH3]O[SiH3].ClCCl.CO.N>C1COCC1>[OH:26][CH:27]1[CH2:28][CH2:29][N:30]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([NH:40][C:16](=[O:18])[C:15]#[C:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:13][N:12]=3)=[CH:36][CH:35]=2)[CH2:31][CH2:32]1

Participants

7

Reactant 5

HCID 123318DisiloxaneHCID 2724141Tetrabutylammonium FluorideHCID 21584172Ammonia methanol dichloromethaneHCID 68816808[5-(4-chlorophenyl)pyridin-2-yl]propynoic AcidHCID 688169094-[4-(Tert-butyldimethylsilanyloxy)piperidin-1-ylmethyl]phenylamine

Product 1

HCID 578457153-[5-(4-Chlorophenyl)pyridin-2-yl]propynoic acid-[4-(4-hydroxypiperidin-1-ylmethyl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 2.3.f. from [5-(4-chlorophenyl)pyridin-2-yl]propynoic acid and 4-[4-(tert-butyldimethylsilanyloxy)piperidin-1-ylmethyl]phenylamine. The cleaving of the silyl group is carried out by adding tetrabutylammonium fluoride to a solution of the silylether in THF. Yield: 0.25 g (43% of theory); melting point: 186° C.-190° C.; C26H24ClN3O2 (M=445.94); calc.: molecular ion peak (M+H)+: 446/448; found: molecular ion peak (M+H)+: 446/448; Rf value: 0.6 (silica gel, dichloromethane/methanol/ammonia (90:10:0.1)).

Workup

  1. customPrepared analogously to Example 2.3.f

Sources & evidence

ORD record
ord-4cbfe1198961458581a58cc1efc62848
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Linked notes

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