Hydrochloric Acid → HCID 90052277, compound

HRID 2284724Notes

Reaction equation

HRID 2284724 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][C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:40])[C@@H:29]([N:31](C)[C:32](=O)OC(C)(C)C)[CH3:30])[CH:24]=[CH:25][CH:26]=3)=[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][C:21]3[CH:22]=[C:23]([NH:27][C:28](=[O:40])[C@@H:29]([NH:31][CH3:32])[CH3:30])[CH:24]=[CH:25][CH:26]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90051759HCID 90051759, compound

Product 1

HCID 90052277HCID 90052277, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-tert-butyl (1-((3-((2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)ethynyl)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (G2, 265 mg) in 1,4-dioxane (4 mL), a 4.0 mol/L solution of hydrochloric acid in 1,4-dioxane (4 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. To the obtained residue, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, and washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then the solvent was evaporated under reduced pressure. The obtained solid matter was recrystallized from a mixed solvent of ethyl acetate and methanol to obtain (S)—N-(3-((2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)ethynyl)phenyl)-2-(methylamino)propanamide (G3, 105 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the obtained residue, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained solid matter was recrystallized from a mixed solvent of ethyl acetate and methanol

Sources & evidence

ORD record
ord-66d1ff80bfed4df7a3937041096bf3df
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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