Sodium Carbonate → HCID 136359933, compound

HRID 1969724Notes

Reaction equation

[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17](S(C5C=CC(C)=CC=5)(=O)=O)[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@H:5]([O:30][C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)[CH2:4]1)[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@H:5]([O:30][C:31]2[CH:32]=[CH:33][C:34]([C:35]#[N:36])=[CH:37][CH:38]=2)[CH2:4]1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-((1R,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclo-pentyloxy)benzonitrile (0.826 g, 1.57 mmol) in 1,4-dioxane (16 mL) was added Na2CO3 (2 N aqueous solution, 16 mL, 31 mmol). The reaction mixture was heated at about 80° C. for about 16 h. The layers were separated and the aqueous portion was extracted with EtOAc (3×40 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (2×30 mL), brine (30 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The residue was purified by using General Procedure AA (Table 2, Method 17, Rt=19.2 min, or =negative) to give 4-((1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)benzonitrile (0.298 g, 51%): LC/MS (Table 1, Method b) Rt=2.07 min; MS m/z: 373 (M+H)+.

Workup

customThe layers were separated
extractionthe aqueous portion was extracted with EtOAc (3×40 mL)
washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×30 mL), brine (30 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customThe residue was purified

Sources & evidence

ORD record: ord-e9e55168ad274ac18ec592992f77d10e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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