Hydrochloric Acid → HCID 117875455, compound

HRID 2283404Notes

Reaction equation

HRID 2283404 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:11]C(=O)OC(C)(C)C)[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=1)=[O:21].Cl.O1CCOCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:11])[CH2:9][CH3:10])=[C:4]([F:19])[C:3]=1[C:20]([C:22]1[CH:23]=[N:24][C:25]([S:28][CH3:29])=[N:26][CH:27]=1)=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89544846HCID 89544846, compound

Product 1

HCID 117875455HCID 117875455, compoundYield 125.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 3 To a solution of tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{[2-(methylsulfanyl)pyrimidin-5-yl]carbonyl}phenyl)propyl]carbamate (20.0 mg, 0.04 mmol) in DCM (1 mL) was added 4M HCl in dioxane (0.04 mL, 0.16 mmol, 4 eq) and the reaction stirred for 18 h. The mixture was concentrated and then triturated with diethyl ether (˜5 mL) and the pale green solid filtered off and dried in a vacuum oven to give (1R)-1-(4-chloro-2-fluoro-3-{[2-(methylsulfanyl)pyrimidin-5-yl]carbonyl}phenyl)propan-1-amine (17.0 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated with diethyl ether (˜5 mL)
  3. filtrationthe pale green solid filtered off
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-cbefc18b27dc4306b9a477d1a2e0c80e
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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