Hydrochloric Acid → HCID 90051752, compound

HRID 2284715Notes

Reaction equation

HRID 2284715 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:37])[C@@H:26]([N:28](C)[C:29](=O)OC(C)(C)C)[CH3:27])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:37])[C@@H:26]([NH:28][CH3:29])[CH3:27])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90051750HCID 90051750, compound

Product 1

HCID 90051752HCID 90051752, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-tert-butyl (1-((5-(2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (F5, 103 mg) in 1,4-dioxane (2 mL), a 4.0 mol/L solution of hydrochloric acid in 1,4-dioxane (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. The solvent was evaporated under reduced pressure. The obtained solid matter was washed with ethyl acetate, and then dried under reduced pressure to obtain (S)—N-(5-(2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)-2-(methylamino)propanamide (F6) dihydrochloride (94 mg) as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washThe obtained solid matter was washed with ethyl acetate
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-07efddfea0454833b5319ab3fa506c03
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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