Pyridine → HCID 59608013, compound

HRID 2191385Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:8][CH2:9][C:10]([C@H:12]2[C@H:19]3[C@H:15]([O:16][C:17]([CH3:21])([CH3:20])[O:18]3)[CH2:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.N1C=CC=CC=1.C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([C@H:12]3[C@H:19]4[C@H:15]([O:16][C:17]([CH3:21])([CH3:20])[O:18]4)[CH2:14][CH2:13]3)=[CH:9][N:8]=2)[CH:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(3-chloropyrazin-2-ylamino)-1-((3aS,4R,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)ethanone (2-8) (1.2 g, 3.85 mmol, 1 equiv) was dissolved in toluene (28 mL) and the mixture was cooled to 0° C. Pyridine (3.74 mL, 46.2 mmol, 12 equiv) was added followed by TFA (2.08 mL, 26.9 mmol, 7 equiv). After 30 minutes, TFAA (3.81 mL, 26.9 mmol, 7 equiv) was added. The resulting mixture was stirred for 1 h, then was concentrated and the yellow residue was purified via flash chromatography on a silica gel column (ethyl acetate/hexanes) to yield desired 8-chloro-3-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (2-9) as a white solid. 1H NMR (500 MHz, CDCl3): δ 8.19 (d, J=4.6 Hz, 1H); 7.84 (d, J=4.6 Hz, 1H); 7.67 (s, 1H); 4.81 (d, J=5.2 Hz, 1H); 4.57 (dd, J=6.0, 2.6 Hz, 1H); 3.47 (s, 1H); 2.52-2.41 (m, 1H); 2.09-2.05 (m, 3H); 1.58 (s, 3H); 1.34 (s, 3H). LRMS m/z (M+H) 293.9 found, 294.1 required.

Workup

concentrationwas concentrated
customthe yellow residue was purified via flash chromatography on a silica gel column (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-81389b285ee248c4b803988394fecac1
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

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