Triethylamine → 4-({[3,5-Dicyano-4-(4-fluorophenyl)-6-(3-hydroxyazetidin-1-yl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide

HRID 714482Notes

Reaction equation

HRID 714482 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:3]=1[C:29]#[N:30].Cl.[NH:32]1[CH2:35][CH:34]([OH:36])[CH2:33]1.C(N(CC)CC)C>CN(C=O)C>[C:20]([C:5]1[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)=[N:7][C:2]([N:32]2[CH2:35][CH:34]([OH:36])[CH2:33]2)=[C:3]([C:29]#[N:30])[C:4]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 866919144-({[6-Chloro-3,5-dicyano-4-(4-fluorophenyl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide

Product 1

HCID 666320744-({[3,5-Dicyano-4-(4-fluorophenyl)-6-(3-hydroxyazetidin-1-yl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.12 mmol) of 4-({[6-chloro-3,5-dicyano-4-(4-fluorophenyl)pyridin-2-yl]oxy}methyl)-N-methylpyridine-2-carboxamide Example 81A were initially charged in 1.5 ml of DMF. After addition of 26 mg (0.24 mmol) of azetidin-3-ol hydrochloride and 24 mg (0.24 mmol) of triethylamine, the mixture was stirred at RT overnight. The reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. customThe reaction mixture was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-b54e12d80de64107bc76199586014622
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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