Hydrochloric Acid → HCID 118023107, compound

HRID 522696Notes

Reaction equation

HRID 522696 reaction equation
CC(C)([S@@]([NH:6][C:7]([C:16]1[CH:17]=[N:18][C:19]([N:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[N:20][CH:21]=1)([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH3:8])=O)C.Cl>O1CCOCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C@@:7]([C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[N:20][CH:21]=2)([NH2:6])[CH3:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118023290HCID 118023290, compound

Product 1

HCID 118023107HCID 118023107, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(5-(1-((S)-1,1-dimethylethylsulfinamido)-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazine-1-carboxylate (2.5 g, 5.0 mmol) in dioxane (5.0 mL) was dropwise added HCl (4M in dioxane, 10 mL). The reaction solution was stirred at room temperature overnight. Then the solution was concentrated under vacuo to give the title compound (1.5 g, crude yield 100%) as a yellow solid. MS (ES+) C16H20FN5 requires: 301, found 302 [M+H]+; purity: 100% (UV at 254 nm). The above racemate (1.5 g) was separated by Chiral-HPLC to afford the desired single enantiomer (600 mg, 40%) as a yellow solid. MS (ES+) C16H20FN5 requires: 301, found: 302 [M+H]+.

Workup

  1. concentrationThen the solution was concentrated under vacuo

Sources & evidence

ORD record
ord-3c1cd2874fc943c29ea86adbf3275acf
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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