Hydrochloric Acid → HCID 44189703, compound

HRID 2191387Notes

Reaction equation

Cl.CC1(C)[O:7][C@@H:6]2[CH2:8][CH2:9][C@@H:10]([C:11]3[N:15]4[CH:16]=[CH:17][N:18]=[C:19]([NH2:20])[C:14]4=[N:13][CH:12]=3)[C@@H:5]2[O:4]1>CO>[NH2:20][C:19]1[C:14]2[N:15]([C:11]([C@@H:10]3[CH2:9][CH2:8][C@@H:6]([OH:7])[C@H:5]3[OH:4])=[CH:12][N:13]=2)[CH:16]=[CH:17][N:18]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Concentrated HCl (4 mL) was added to 3-((3aS,4S,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (2-10) (1.20 g, 4.37 mmol, 1 equiv) in methanol (20 mL) and the mixture was heated to 65° C. After 8 hours, no more starting material was present and the mixture was concentrated to afford desired (1R,2S,3S)-3-(8-aminoimidazo[1,2-a]pyrazin-3-yl)cyclopentane-1,2-diol (2-11) as a tan solid. 1H NMR (500 MHz, CD3 OD): δ 8.06 (d, J=5.8 Hz, 1H); 7.82 (s, 1H); 7.27 (d, J=5.7 Hz, 1H); 4.14 (s, 1H); 4.04 (dd, J=9.3, 4.5 Hz, 1H); 3.55 (q, J=9.1 Hz, 1H); 2.40-2.29 (m, 1H); 2.22-2.10 (m, 1H); 1.92-1.80 (m, 2H). LRMS m/z (M+H) 235.1 found, 235.1 required.

Workup

concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-76aa1e2b196041eba4541cf01df52646
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329697B2

Reaction notes

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