Hydrochloric Acid → 3-Ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine

HRID 1854449Notes

Reaction equation

HRID 1854449 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH:11]([C:13]2[N:17]3[C:18]4[CH:24]=[CH:23][N:22]([S:25]([C:28]5[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=5)(=[O:27])=[O:26])[C:19]=4[N:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH:10]([CH2:35][CH3:36])[CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[CH2:35]([CH:10]1[CH:11]([C:13]2[N:17]3[C:18]4[CH:24]=[CH:23][N:22]([S:25]([C:28]5[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=5)(=[O:27])=[O:26])[C:19]=4[N:20]=[CH:21][C:16]3=[N:15][N:14]=2)[CH2:12][CH:8]([NH2:7])[CH2:9]1)[CH3:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58010142tert-butyl-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate

Product 1

HCID 580098883-Ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamineYield 68.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A round-bottomed flask was charged with tert-butyl-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate (1.7 g, 3.2 mmol) and 1,4-dioxane (20 mL) to give a brown solution. HCl (4 N in 1,4-dioxane, 4.05 mL, 16.2 mmol) was added and the mixture was stirred at about 40° C. for about 3 h. The solvent was removed under reduced pressure. EtOAc (50 mL) and saturated aqueous NaHCO3 (20 mL) were added. The resulting solid was collected by vacuum filtration and dried on the lyophilizer to give a grey solid (0.93 g). The layers of the filtrate were partitioned and the aqueous layer was extracted with EtOAc (3×40 mL). The organic layer was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to give a brown residue (0.52 g). The material obtained was combined to give 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1, 2, 4]triazolo[4,3-a]pyrazin-1-yl)cyclopenta amine (1.45 g, 80% UV purity, 84%): LC/MS (Table 2, Method a) Rt=1.76 min; MS m/z: 425 (M+H)+.

Workup

  1. customto give a brown solution
  2. customThe solvent was removed under reduced pressure
  3. additionEtOAc (50 mL) and saturated aqueous NaHCO3 (20 mL) were added
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. customdried on the lyophilizer

Sources & evidence

ORD record
ord-bd0b7fad143e4a44abf7821f19d82c31
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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