Diisopropylethylamine → N-(2-Cyano-ethyl)-N-isopropyl-3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

HRID 2268669Notes

Reaction equation

HRID 2268669 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)[C:12]([OH:14])=O.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH:61]([NH:64][CH2:65][CH2:66][C:67]#[N:68])([CH3:63])[CH3:62]>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:67]([CH2:66][CH2:65][N:64]([CH:61]([CH3:63])[CH3:62])[C:12](=[O:14])[C:11]1[CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=[C:9]([CH3:8])[CH:10]=1)#[N:68]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1364943-[(Propan-2-yl)amino]propanenitrileHCID 2733179PyBroP2×HCID 699496943-Methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate

Product 1

HCID 18349097N-(2-Cyano-ethyl)-N-isopropyl-3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate salt (0.026 g) in anhydrous DMF (2 ml) was treated at room temperature with 3-isopropylamino-propionitrile9 (0.017 g), PyBrop® (0.062 g) and DIPEA (0.025 ml). More PyBrop® was added after 2 days (0.072 g) and 7 days (0.065 g). More 3-isopropylamino-propionitrile was added after 2 days (0.03 ml), 4 days (0.1 ml) and 7 days (0.1 ml). After 24 h more, the mixture was evaporated to dryness under reduced pressure and the residue subjected to preparative hplc giving the title compound as a clear colourless gum (0.016 g).

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f0276bdb4d174120ab17d366ba8aeb27
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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