1,1'-Carbonyldiimidazole → HCID 58557568, compound

HRID 1969599Notes

Reaction equation

HRID 1969599 reaction equation
[CH:1]1([CH2:4][CH2:5][NH2:6])[CH2:3][CH2:2]1.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>[CH:1]1([CH2:4][CH2:5][NH:6][C:12]([N:24]2[CH2:23][C@H:22]([C:26]3[N:30]4[C:31]5[CH:37]=[CH:36][N:35]([S:38]([C:41]6[CH:42]=[CH:43][C:44]([CH3:45])=[CH:46][CH:47]=6)(=[O:40])=[O:39])[C:32]=5[N:33]=[CH:34][C:29]4=[N:28][N:27]=3)[C@H:21]([CH2:19][CH3:20])[CH2:25]2)=[O:13])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 10240761CyclopropaneethanamineHCID 67216364HCID 67216364, compound

Product 1

HCID 58557568HCID 58557568, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-cyclopropylethanamine (0.068 g, 0.804 mmol, Oakwood) in DMF (3 mL) was added CDI (0.150 g, 0.926 mmol). The 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, Example #36, step F) was added and the reaction mixture continued heating at about 65° C. After about 2 h, the reaction mixture was cooled to ambient temperature. The solvent was removed under reduced pressure. The crude material was purified by chromatography on silica gel eluting with a gradient of 0-10% MeOH in DCM to give (cis)-N-(2-cyclopropylethyl)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)pyrrolidine-1-carboxamide (0.238 g, 64%) as product: LC/MS (Table 1, Method a) Rt=2.17 min; MS m/z: 522 (M+H)+.

Workup

  1. temperaturethe reaction mixture continued heating at about 65° C
  2. waitAfter about 2 h
  3. temperaturethe reaction mixture was cooled to ambient temperature
  4. customThe solvent was removed under reduced pressure
  5. customThe crude material was purified by chromatography on silica gel eluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-530b343428824d869924b76a2441b8e5
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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