Hydrochloric Acid → HCID 67435312, compound
Reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH2:19][NH:20]C(=O)OC(C)(C)C)[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl>C(O)C>[NH2:20][CH2:19][C@@H:15]1[N:14]2[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:18][O:17][CH2:16]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
tert-Butyl [(11S)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]methylcarbamate (1.39 g, 3.77 mmol) was dissolved in 10 mL of ethanol and 3 mL of a 4.3 M solution of HCl in ethanol was added. The reaction mixture was heated to 85° C. After 1 hour, the reaction mixture was concentrated under reduced pressure. The resulting residue was treated with 40 mL of H2O and 20 mL of CHCl3. The layers were separated and the organic portion was discarded. The aqueous layer was then made basic by addition of 5 mL of concentrated NH4OH solution. The aqueous portion was then extracted with CHCl3 (15×20 mL). The combined organic extracts were concentrated under reduced pressure to give (11S)-11-(aminomethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (778 mg) as a pumpkin colored solid.
Workup
- concentrationthe reaction mixture was concentrated under reduced pressure
- additionThe resulting residue was treated with 40 mL of H2O and 20 mL of CHCl3
- customThe layers were separated
- additionThe aqueous layer was then made basic by addition of 5 mL of concentrated NH4OH solution
- extractionThe aqueous portion was then extracted with CHCl3 (15×20 mL)
- concentrationThe combined organic extracts were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-6b4d8adb19914c9cb647b4effe444553
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08350034B2
Reaction notes
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