Ethanamine, 2,2,2-trifluoro- → HCID 67216455, compound

HRID 1969893Notes

Reaction equation

HRID 1969893 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].C1N=CN([C:12](N2C=NC=C2)=[O:13])C=1.[CH2:19]([C@H:21]1[CH2:25][NH:24][CH2:23][C@H:22]1[C:26]1[N:30]2[C:31]3[CH:37]=[CH:36][N:35]([S:38]([C:41]4[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=4)(=[O:40])=[O:39])[C:32]=3[N:33]=[CH:34][C:29]2=[N:28][N:27]=1)[CH3:20]>CN(C=O)C>[CH2:19]([C@H:21]1[C@@H:22]([C:26]2[N:30]3[C:31]4[CH:37]=[CH:36][N:35]([S:38]([C:41]5[CH:42]=[CH:43][C:44]([CH3:45])=[CH:46][CH:47]=5)(=[O:40])=[O:39])[C:32]=4[N:33]=[CH:34][C:29]3=[N:28][N:27]=2)[CH2:23][N:24]([C:12]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[O:13])[CH2:25]1)[CH3:20]

Participants

5

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 682631,1'-CarbonyldiimidazoleHCID 67216364HCID 67216364, compound

Product 1

HCID 67216455HCID 67216455, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2,2,2-trifluoroethanamine (0.080 g, 0.804 mmol) in DMF (3 mL) was added CDI (0.150 g, 0.926 mmol). The resulting solution was stirred at about 65° C. for about 2 h. 1-((cis)-4-ethylpyrrolidin-3-yl)-6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.250 g, 0.609 mmol) was added and the reaction continued stirring at about 65° C. for about 2 h. The reaction was cooled to about ambient temperature. The solvent was removed under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a gradient of 0-10% MeOH in afford (cis)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide (0.306 g, 94%) as a brown residue: LC/MS (Table 1, Method a) Rt=2.19 min; MS m/z: 536 (M+H)+.

Workup

  1. stirringthe reaction continued stirring at about 65° C. for about 2 h
  2. temperatureThe reaction was cooled to about ambient temperature
  3. customThe solvent was removed under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica gel eluting with a gradient of 0-10% MeOH in afford (cis)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide (0.306 g, 94%) as a brown residue

Sources & evidence

ORD record
ord-9e31d51112584d05aa85fa4b471a4ae4
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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