Sodium Hydroxide → HCID 136349136, compound

HRID 2204492Notes

Reaction equation

HRID 2204492 reaction equation
S([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([NH:20][NH:21][C:22]([C@@H:24]3[CH2:28][CH2:27][C@@H:26]([CH2:29][NH:30]C(=O)OC(C)(C)C)[CH2:25]3)=O)[N:19]=[C:14]2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.C(OC(NC[C@@H]1CC[C@@H](C(O)=O)C1)=O)(C)(C)C.CCN(C(C)C)C(C)C.O=S(Cl)[Cl:66].[OH-].[Na+]>O1CCOCC1>[ClH:66].[C:22]1([C@@H:24]2[CH2:28][CH2:27][C@@H:26]([CH2:29][NH2:30])[CH2:25]2)[N:19]2[C:14]3[CH:13]=[CH:12][NH:11][C:15]=3[N:16]=[CH:17][C:18]2=[N:20][N:21]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 58009849HCID 58009849, compoundHCID 69014000(1R,3R)-3-[[[(1,1-Dimethylethoxy)carbonyl]amino]methyl]cyclopentanecarboxylic acid

Product 1

HCID 136349136HCID 136349136, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl ((1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentyl)methylcarbamate (0.60 g, 1.1 mmol, prepared using A from (1R,3R)-3-((tert-butoxycarbonylamino)methyl)cyclopentanecarboxylic acid [AFID] and Preparation #9) and DIEA (0.79 mL, 4.5 mmol) in 1,4-dioxane (5 mL) was added SOCl2 (0.166 mL, 2.27 mmol). The reaction mixture was heated at about 80° C. for about 1 h before it was allowed to cool to ambient temperature. Aqueous NaOH (2 N, 4 mL, 8 mmol) was added to the reaction mixture and heated at about 60° C. for about 2 h. The reaction mixture was allowed to cool to ambient temperature before it was concentrated under reduced pressure. To the residue was added HCl (4N in 1,4-dioxane (20 mL). The organic solution was decanted away from the resulting precipitate to afford ((1R,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)methanamine hydrochloride as a yellow solid (0.11 g, 33%): LC/MS (Table 2, Method a) Rt=1.01 min; MS m/z: 257 (M+H)+.

Workup

  1. temperatureto cool to ambient temperature
  2. temperatureheated at about 60° C. for about 2 h
  3. temperatureto cool to ambient temperature before it
  4. concentrationwas concentrated under reduced pressure
  5. additionTo the residue was added HCl (4N in 1,4-dioxane (20 mL)
  6. customThe organic solution was decanted away from the resulting precipitate

Sources & evidence

ORD record
ord-ad45310c7bc541dd943d3698aac8dae0
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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