Hydrochloric Acid → HCID 118389991, compound

HRID 1478050Notes

Reaction equation

HRID 1478050 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.[NH2:25][C:26]1[CH:27]=[N:28][N:29]([CH2:31][CH2:32][OH:33])[CH:30]=1.Cl>CC(O)C>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:25][C:26]2[CH:27]=[N:28][N:29]([CH2:31][CH2:32][OH:33])[CH:30]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Product 1

HCID 118389991HCID 118389991, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
140 °C

Procedure

To a suspension of tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (633.5 mg, 1.70 mmol) and 2-(4-amino-1H-pyrazol-1-yl)ethanol (249.1 mg, 1.99 mmol) in i-PrOH (8 mL) was added a solution of HCl in EtOAC ((1 mL, 4 mmol)). The reaction mixture was stirred at 140° C. under microwave radiation for 1 h and concentrated in vacuo. The residue was dissolved in water (30 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (100 mL×3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30) to give the title compound as a yellow solid (0.50 g, 63%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (30 mL)
  3. extractionextracted with DCM (100 mL×3)
  4. washThe combined organic phases were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/30)

Sources & evidence

ORD record
ord-ea78df19d8bd49e8a2d111a5d1fce791
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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