Ammonia → HCID 67285565, compound

HRID 2191377Notes

Reaction equation

HRID 2191377 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)[C:14]([CH2:22][O:23][C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:13]3)=[CH:10][N:11]=2)[CH:6]=[CH:7][N:8]=1>C(O)(C)C>[CH3:21][C:17]1([CH3:20])[O:16][C@@H:15]2[C:14]([CH2:22][O:23][C:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH: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

4

Reactant 2

HCID 222AmmoniaHCID 86648186HCID 86648186, compound

Product 1

HCID 67285565HCID 67285565, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

Liquid ammonia (10 mL) was added to 8-chloro-3-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazine (1-8) (180 mg, 0.32 mmol, 1 equiv) in isopropanol (10 mL). The resulting solution was placed in a high pressure vessel and heated to 100° C. (pressure did not exceed 600 psi) for 20 h. The resulting amber solution was concentrated, and the residue was purified via reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to afford 3-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (1-9) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.7 (d, 1H, J=5.5 Hz), 7.21-7.50 (m, 17H), 6.06 (s, 1H), 5.19 (d, 1H, J=5.5 Hz), 4.66 (d, 1H, J=5.5 Hz), 4.33 (m, 1H), 3.91 (d, 1H, J=14 Hz), 3.83 (d, 1H, J=14 Hz), 1.43 (s, 3H), 1.33 (s, 3H). LRMS m/z (M+H) 544.9 found, 545.2 required.

Workup

  1. customThe resulting solution was placed in a high pressure vessel
  2. customfor 20 h
  3. concentrationThe resulting amber solution was concentrated
  4. customthe residue was purified via reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-72f542c4ee8d427fb6b06592d829ed5a
Source dataset
uspto-grants-2012_12
Patent number
US08329697B2

Reaction notes

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