Hydrochloric Acid → HCID 66705787, compound

HRID 2276388Notes

Reaction equation

HRID 2276388 reaction equation
[F:1][C:2]([F:34])([F:33])[CH2:3][O:4][C:5]1[CH:32]=[CH:31][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[O:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]3)=[CH:14][CH:13]=2)=[O:10])=[CH:7][N:6]=1.[ClH:35]>O1CCOCC1>[ClH:35].[NH:20]1[CH2:21][CH2:22][O:23][C@@H:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:31]=[CH:32][C:5]([O:4][CH2:3][C:2]([F:1])([F:33])[F:34])=[N:6][CH:7]=3)=[CH:17][CH:16]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66705899HCID 66705899, compound

Product 1

HCID 66705787HCID 66705787, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of (S)-tert-butyl 2-(4-(6-(2,2,2-trifluoroethoxy)nicotinamido)phenyl)morpholine-4-carboxylate (2.11 g) in dioxane (8 ml) was added dropwise a solution of hydrogen chloride in dioxane (16.7 ml, 4 M solution) and the mixture was heated at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with dioxane, and the crystalline product was collected by filtration, washing with Et2O. The product was dried in vacuo to afford (S)—N-(4-(morpholin-2-yl)phenyl)-6-(2,2,2-trifluoroethoxy)nicotinamide hydrochloride (1.75 g, 94%) as a light yellow solid. MS (ISP): 382.2 ([M+H]+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe crystalline product was collected by filtration
  3. washwashing with Et2O
  4. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-449b338ac6ca4c59b14c1e1b6a9109cf
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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