3,3,3-Trifluoropropylamine → HCID 68764687, compound

HRID 1968327Notes

Reaction equation

HRID 1968327 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.[F:36][C:37]([F:42])([F:41])[CH2:38][CH2:39][NH2:40]>CN(C=O)C.O.C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[S:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:15]=4)[C:7]([C:8]#[N:9])=[C:2]([NH:40][CH2:39][CH2:38][C:37]([F:42])([F:41])[F:36])[N:3]=3)[N:25]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 100013,3,3-TrifluoropropylamineHCID 866438472-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 68764687HCID 68764687, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 100° C., 150 mg (0.21 mmol, purity about 74%) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 93 mg (0.82 mmol) of 3,3,3-trifluoropropan-1-amine were stirred in 2.0 ml of DMF for 2 h. The reaction mixture was then diluted with about 1 ml of water and about 3 ml of THF and purified by preparative HPLC (acetonitrile/water+0.1% TFA). This gave 105 mg (83% of theory) of the target compound.

Workup

  1. custompurified by preparative HPLC (acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-99f95124759f45f09eda5b8d211744fe
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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