Hydrochloric Acid → HCID 136349069, compound
Reaction equation
[C:1]1([C@@H:13]2[CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[N:3][N:2]=1.C(OC(N1CCC[C@@H](C(O)=O)C1)=O)(C)(C)C.O=S(Cl)[Cl:44].C([O-])([O-])=O.[Na+].[Na+].Cl>O1CCOCC1.C(Cl)CCl>[ClH:44].[NH:15]1[CH2:16][CH2:17][CH2:18][C@@H:13]([C:1]2[N:5]3[C:6]4[CH:12]=[CH:11][NH:10][C:7]=4[N:8]=[CH:9][C:4]3=[N:3][N:2]=2)[CH2:14]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A round bottom flask was charged with (R)-tert-butyl 3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)piperidine-1-carboxylate (0.92 g, 2.68 mmol; prepared using A from Preparation #9, (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid [CNH Technologies], EDC and TEA, and E using SOCl2, TEA, and saturated aqueous Na2CO3), HCl (4 N in 1,4-dioxane, 2.9 mL, 11.5 mmol), and 1,4-dioxane (20 mL). The reaction mixture was heated at about 60° C. for about 3 h. The reaction mixture was cooled to ambient temperature then filtered under vacuum and washed with Et2O (35 mL). The solid was then dried for about 16 h in a heated vacuum oven (at about 70° C.) to give (R)-1-(piperidin-3-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine hydrochloride as a brown solid (0.69 g, 82%): LC/MS (Table 2, Method a) Rt=0.45 min; MS m/z 243 (M+H)+.
Workup
- customprepared
- temperatureThe reaction mixture was cooled to ambient temperature
- filtrationthen filtered under vacuum
- washwashed with Et2O (35 mL)
- customThe solid was then dried for about 16 h in a heated vacuum oven (at about 70° C.)
Sources & evidence
- ORD record
- ord-93f8bdad7af549afbfab0b2d797e415f
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365579B2
Reaction notes
Loading…