Hydrochloric Acid → HCID 136349069, compound

HRID 1854344Notes

Reaction equation

HRID 1854344 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]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylateHCID 136199057HCID 136199057, compound

Product 1

HCID 136349069HCID 136349069, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

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

  1. customprepared
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationthen filtered under vacuum
  4. washwashed with Et2O (35 mL)
  5. customThe solid was then dried for about 16 h in a heated vacuum oven (at about 70° C.)

Sources & evidence

ORD record
ord-f0e609c325744d9ab0b4c7d40623e3ad
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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