Ammonia → HCID 59608014, compound

HRID 2191386Notes

Reaction equation

[NH3:1].Cl[C:3]1[C:4]2[N:5]([C:9]([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:10][N:11]=2)[CH:6]=[CH:7][N:8]=1>C(O)(C)C>[CH3:20][C:17]1([CH3:21])[O:16][C@@H:15]2[CH2:14][CH2:13][C@@H:12]([C:9]3[N:5]4[CH:6]=[CH:7][N:8]=[C:3]([NH2:1])[C:4]4=[N:11][CH:10]=3)[C@@H:19]2[O:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

Liquid ammonia (50 mL) was added to 8-chloro-3-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (2-9) (1.5 g, 5.1 mmol, 1 equiv) in isopropanol (50 mL). The resulting solution was placed in a high pressure vessel and heated to 100° C. After 16 hours, no more starting material was present, the amber solution was concentrated to afford desired 3-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (2-10) as a tan solid that was carried to the next step without further purification. 1H NMR (500 MHz, CDCl2): δ 7.50 (d, J=4.7 Hz, 1H); 7.36 (t, J=4.6 Hz, 1H); 7.23 (s, 1H); 5.60 (s, 2H); 4.78 (s, 1H); 4.64 (d, J=5.7 Hz, 1H); 3.44 (d, J=6.9 Hz, 1H); 2.43-2.33 (m, 1H); 2.04-1.93 (m, 3H); 1.55 (s, 3H); 1.34 (s, 3H). LRMS m/z (M+H) 275.0 found, 275.1 required.

Workup

customThe resulting solution was placed in a high pressure vessel
concentrationthe amber solution was concentrated

Sources & evidence

ORD record: ord-badbbb750e904fc8bac98ff845483d6e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

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