Ethynylpyridine → N-((R)-2-Cyclopropyl-2-hydroxy-propyl)-6-(2-pyridin-2-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

HRID 1929930Notes

Reaction equation

HRID 1929930 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].CO[C:11](=[O:29])[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[C:15](Cl)=[N:14][CH:13]=1.[NH2:30][CH2:31][C@@:32]([CH3:37])([CH:34]1[CH2:36][CH2:35]1)[OH:33]>>[CH:34]1([C@:32]([OH:33])([CH3:37])[CH2:31][NH:30][C:11](=[O:29])[C:12]2[CH:17]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=3)[C:15]([CH2:2][CH2:1][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)=[N:14][CH:13]=2)[CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 137268EthynylpyridineHCID 51684102(2R)-1-amino-2-cyclopropyl-propan-2-olHCID 866195756-Chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester

Product 1

HCID 24797711N-((R)-2-Cyclopropyl-2-hydroxy-propyl)-6-(2-pyridin-2-yl-ethyl)-5-(4-trifluoromethyl-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 140, using 2-ethynyl-pyridine (CAN 1945-84-2), 6-chloro-5-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester, and (R)-α-(aminomethyl)-α-methyl-cyclopropanemethanol as starting materials, LC at 215 nm; Rt 3.30: 98%, m/z (ES+): 470.5 (M+H).

Workup

  1. customdescribed for the preparation of Example 140

Sources & evidence

ORD record
ord-66a6f00a8b314869a1fc4f7a825801c1
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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