Diisopropylethylamine → Trifluoroacetic acid

HRID 521241Notes

Reaction equation

HRID 521241 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:33][C:34]([F:39])([F:38])[C:35]([O-:37])=[O:36].[C:40]([C:43]1[C:44]([NH:57][C:58]2[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=2)=[N:45][N:46]([C:48]2([CH2:54][C:55]#[N:56])[CH2:53][CH2:52][NH2+:51][CH2:50][CH2:49]2)[CH:47]=1)(=[O:42])[NH2:41].CCN(C(C)C)C(C)C>CN(C=O)C>[C:35]([OH:37])([C:34]([F:39])([F:38])[F:33])=[O:36].[C:55]([CH2:54][C:48]1([N:46]2[CH:47]=[C:43]([C:40]([NH2:41])=[O:42])[C:44]([NH:57][C:58]3[CH:59]=[CH:60][C:61]([F:64])=[CH:62][CH:63]=3)=[N:45]2)[CH2:53][CH2:52][N:51]([C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])[CH2:50][CH2:49]1)#[N:56]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867294014-(4-carbamoyl-3-((4-fluorophenyl)amino)-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidin-1-ium 2,2,2-trifluoroacetate2×

Product 2

HCID 6422Trifluoroacetic acidHCID 867294171-(4-(Cyanomethyl)-1-(3,3,3-trifluoropropanoyl)piperidin-4-yl)-3-(4-fluorophenylamino)-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3,3,3-Trifluoropropanoic acid (0.009 mL, 0.1 mmol) and HATU (40 mg, 0.11 mmol) were combined in DMF (0.15 mL) and allowed to stir at ambient temperature for 5 minutes. A solution of 4-{4-carbamoyl-3-[(4-fluorophenyl)amino]-1H-pyrazol-1-yl}-4-(cyanomethyl)piperidinium trifluoroacetate (Intermediate #38-5) (30 mg, 0.066 mmol) in DMF (0.10 mL) was then added to the reaction mixture, followed by DIPEA (0.045 mL, 0.26 mmol). The resulting solution was allowed to stir at ambient temperature for 16 hours. The mixture was then purified directly by mass-triggered reverse-phase preparative HPLC (MeCN/water, with 0.1% v/v TFA modifier) to afford the title compound, Example #35-1.

Workup

  1. stirringto stir at ambient temperature for 16 hours
  2. customThe mixture was then purified directly by mass-triggered reverse-phase preparative HPLC (MeCN/water

Sources & evidence

ORD record
ord-06c61c675a614ba2bd1d517aad6a3682
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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