Cyanoacetic acid → HCID 58557214, compound

HRID 1969619Notes

Reaction equation

HRID 1969619 reaction equation
[O:1]=[CH:2][CH2:3][C:4]#[N:5].[F:6][C:7]([F:18])([F:17])[C:8]1[C:13]([C:14](O)=O)=[CH:12][N:11]=[CH:10][CH:9]=1.CN(C(O[N:27]1N=[N:34][C:29]2C=[CH:31][CH:32]=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1.[OH-].[Na+].[C:76]([CH2:78][C:79](O)=O)#[N:77]>CS(C)=O.CO.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[C:14]1([C@@H:13]2[C@H:8]([C:7]([F:18])([F:17])[F:6])[CH2:9][CH2:10][N:11]([C:2](=[O:1])[CH2:3][C:4]#[N:5])[CH2:12]2)[N:34]2[C:29]3[CH:31]=[CH:32][NH:33][C:28]=3[N:27]=[CH:79][C:78]2=[CH:76][N:77]=1

Participants

10

Reactant 7

HCID 9740Cyanoacetic acidHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine2×HCID 87949Lawesson's reagentHCID 151404CyanoacetaldehydeHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×

Product 1

HCID 58557214HCID 58557214, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 2723924Mercury bis(trifluoroacetate)CatalystHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

A mixture of 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (0.067 g, 0.18 mmol, prepared using O from 4-(trifluoromethyl)nicotinic acid, N, H with Example #5, Step C, HATU and DIEA, Q with Lawesson's reagent and mercury (II) trifluoroacetate, D with NaOH, F, H with 2-cyanoacetic acid, HATU, and DIEA) was dissolved in DMSO:MeOH (2:1, 3 mL). The mixture was separated using Varian 218 LC pumps, a Varian CVM 500 with switching valves and heaters for automatic solvent, column and temperature control and a Varian 701 Fraction collector using Method 4 (Table 2) to give 3-((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (Rt=12.2 min, or =positive) (0.0284 g, 15%) [AA.1.1] and 3-((3S,4S)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrde (Rt=5.3 min, or =negative) (0.0282 g, 15%) [AA.1.2]: LC/MS (Table 1, Method b) Rt=1.55 min; MS m/z: 377 (M+H)+.

Workup

  1. customprepared
  2. customThe mixture was separated

Sources & evidence

ORD record
ord-88c4f64b836243808284e5444abbe14b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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