Hydrochloric Acid → HCID 72706871, compound

HRID 595264Notes

Reaction equation

HRID 595264 reaction equation
Cl.[Si]([O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[CH:21]=[C:22]([C:27]3[CH:28]=[N:29][N:30]([CH2:32][CH2:33][C:34]([NH2:36])=[O:35])[CH:31]=3)[CH:23]=[C:24]([CH3:26])[CH:25]=2)[N:14]=1)(C(C)(C)C)(C)C>C1COCC1.O>[OH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]2[CH:21]=[C:22]([C:27]3[CH:28]=[N:29][N:30]([CH2:32][CH2:33][C:34]([NH2:36])=[O:35])[CH:31]=3)[CH:23]=[C:24]([CH3:26])[CH:25]=2)[N:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131734579HCID 131734579, compound

Product 1

HCID 72706871HCID 72706871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

HCl (550 μL, 0.55 mmol) was added to a solution of 3-[4-(3-{[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]propanamide (91 mg, 0.18 mmol) in THF (1000 μL). The reaction mixture was stirred for 18 h at room temperature then diluted with water and extracted with EtOAc (2×) and chloroform:IPA (3:1). The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure, triturated with dichloromethane:hexanes (1:1) and then purified by reverse phase HPLC (ACN/water with 0.1% formic acid modifier) to afford 3-[4-(3-{[4-(2-hydroxyethoxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]propanamide as a white solid. MS ESI calcd. for C19H23N6O3 [M+H]+ 382. found 382.

Workup

  1. extractionextracted with EtOAc (2×) and chloroform:IPA (3:1)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customtriturated with dichloromethane:hexanes (1:1)
  6. custompurified by reverse phase HPLC (ACN/water with 0.1% formic acid modifier)

Sources & evidence

ORD record
ord-bca4d6e7edfc4e8db7500b0a5232ca2b
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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