HCID 90051715, compound → HCID 90052192, compound

HRID 2284636Notes

Reaction equation

HRID 2284636 reaction equation
[O:1]=[C:2]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]2[C:24]([NH:38][CH2:39][CH2:40][CH3:41])=[N:25][C:26]([NH:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)=[N:27][CH:28]=2)=[O:22])[CH:15]=1)[C@@H:3]([NH:5]C(=O)OC(C)(C)C)[CH3:4]>C(Cl)(Cl)Cl.FC(F)(F)C(O)=O>[NH2:5][C@@H:3]([CH3:4])[C:2]([NH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21]([C:23]2[C:24]([NH:38][CH2:39][CH2:40][CH3:41])=[N:25][C:26]([NH:29][CH2:30][CH2:31][C:32]3[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=3)=[N:27][CH:28]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1)=[O:1]

Participants

4

Reactant 1

HCID 90051715HCID 90051715, compound

Product 1

HCID 90052192HCID 90052192, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (S)-tert-butyl (1-oxo-1-((3-(4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamido)phenyl)amino)propan-2-yl)carbamate (A5, 137 mg) in chloroform (2 mL), trifluoroacetic acid (2 mL) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. The solvent was evaporated under reduced pressure, and to the obtained residue, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate was added, and the solid matter was taken by filtration, and dried under reduced pressure to obtain (S)—N-(3-(2-aminopropanamido)phenyl)-4-(propylamino)-2-((2-(pyridin-4-yl)ethyl)amino)pyrimidine-5-carboxamide (A6, 75 mg) as white solid.

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. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue, ethyl acetate was added
  9. filtrationthe solid matter was taken by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-d6d5c329d6924e12af489f4d3b3b3912
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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