Acetic Acid → N-((1R,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)aniline

HRID 1969709Notes

Reaction equation

S([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].CC(O)=O>O1CCOCC1>[C:20]1([C@@H:23]2[CH2:27][CH2:26][C@@H:25]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24]2)[N:19]2[C:14]3[CH:13]=[CH:12][NH:11][C:15]=3[N:16]=[CH:17][C:18]2=[N:22][N:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To N-((1R,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)aniline (0.106 g, 0.224 mmol) in 1,4-dioxane (1 mL) was added NaOH (1 N aqueous, 1.12 mL, 1.12 mmol). The reaction mixture was heated at about 60° C. for about 1 h. AcOH (0.5 mL) was added and the crude reaction mixture was purified by RP-HPLC (Table 1, Method j) to give N-((1R,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)aniline (0.053 g, 74%) as a light yellow solid: LC/MS (Table 1, Method b) Rt=1.84 min; MS m/z: 319 (M+H)+.

Workup

customthe crude reaction mixture
customwas purified by RP-HPLC (Table 1, Method j)

Sources & evidence

ORD record: ord-094bad1dbc6e4df89380889578835541
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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