Cyclopropylacetylene → 5-(4-Chloro-phenyl)-6-(2-cyclopropyl-ethyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

HRID 505964Notes

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]([CH:27]1[CH2:29][CH2:28]1)#[CH:26]>>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[C:2]([CH2:26][CH2:25][CH:27]3[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 138823Cyclopropylacetylene

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

Product 1

HCID 247974435-(4-Chloro-phenyl)-6-(2-cyclopropyl-ethyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Examples 1d tole, using 6-chloro-5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-nicotinamide and ethynylcyclopropane as starting materials; yield 189 mg, 46% over two steps; m/z (ISP+): 399.2, 401.3 (M+H).

Sources & evidence

ORD record: ord-4d27c0fb05884b8f81db188aaa6a2f6c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781593B2

Reaction notes

Loading…