1-Ethynylcyclopentanol → 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide

HRID 1929908Notes

Reaction equation

Cl[C:2]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:16][C:5]([C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[OH:15])=[O:7])=[CH:4][N:3]=1.[C:25]([C:27]1([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28]1)#[CH:26]>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[C:2]([C:26]#[C:25][C:27]3([OH:32])[CH2:31][CH2:30][CH2:29][CH2:28]3)=[N:3][CH:4]=[C:5]([CH:16]=2)[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[OH:15])=[O:7])=[CH:19][CH:20]=1

Participants

Reactant 2

HCID 870741-Ethynylcyclopentanol

HCID 866191846-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

Product 1

HCID 675049925-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 112, using 6-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide and 1-ethynylcyclopentanol as starting materials to yield the product as colorless solid, MS (ISP) 439.1, 441.2 (M+H)+.

Sources & evidence

ORD record: ord-fa360fef7561470eb7583d506f0b6835
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188093B2

Reaction notes

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