Trifluoroacetic anhydride → HCID 136009369, compound

HRID 1969673Notes

Reaction equation

HRID 1969673 reaction equation
[CH2:1]([CH:3]1[CH:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][CH:5]([CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=O)[CH2:4]1)[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([CH2:20][CH2:21][CH2:22][C:23]#[N:25])[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 136009357HCID 136009357, compound

Product 1

HCID 136009369HCID 136009369, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)butanamide (0.090 g, 0.264 mmol, Example #FFFF.1) in DCM (3 mL) was added TFAA (0.373 mL, 2.64 mmol). After about 4 h at ambient temperature the reaction mixture was concd in vacuo and purified by chiral preparative HPLC (Table 2, Method 33) to provide 4-((1S,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)butanenitrile (0.013 g, 15%) (rt=16.1 min, or =neg) LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z: 323 (M+H)+ and 4-((1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)butanenitrile (0.010 g, 12%) (rt=13.7 min, or =neg) LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z: 323 (M+H)+ as solids.

Workup

  1. custompurified by chiral preparative HPLC (Table 2, Method 33)

Sources & evidence

ORD record
ord-49d64d663aa647ffbda22f9fc38e7dca
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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