Sodium Hydroxide → HCID 136349136, compound

HRID 1854341Notes

Reaction equation

HRID 1854341 reaction equation
C(OC(=O)[NH:7][CH2:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([NH:16][NH:17][C:18]2[N:19]=[C:20]3[CH:26]=[CH:25][N:24](S(C4C=CC(C)=CC=4)(=O)=O)[C:21]3=[N:22][CH:23]=2)=O)[CH2:10]1)(C)(C)C.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:14]1([C@@H:11]2[CH2:12][CH2:13][C@@H:9]([CH2:8][NH2:7])[CH2:10]2)[N:19]2[C:20]3[CH:26]=[CH:25][NH:24][C:21]=3[N:22]=[CH:23][C:18]2=[N:17][N:16]=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-161170fa89a44767ad6a4214afa5f459
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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