HCID 86615799, compound → HCID 67520706, compound

HRID 1787071Notes

Reaction equation

HRID 1787071 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[N:25]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[CH:24]=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Cl:15])[CH:14]=1>O1CCCC1.Cl>[ClH:1].[ClH:1].[ClH:1].[NH2:28][CH2:27][CH2:26][N:25]1[C:18]2[C:17]([NH:16][C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]4[CH:10]=[N:11][CH:12]=[C:13]([Cl:15])[CH:14]=4)=[C:2]([Cl:1])[CH:3]=3)=[N:22][CH:21]=[N:20][C:19]=2[CH:23]=[CH:24]1

Participants

4

Reactant 1

HCID 86615799HCID 86615799, compound

Product 1

HCID 67520706HCID 67520706, compoundYield 372.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl {2-[4-({3-chloro-4-[(5-chloropyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}carbamate (700 mg) was dissolved in tetrahydrofuran (19.5 mL)/2N hydrochloric acid (9.75 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethanol (50 mL) was added to the residue and the mixture was concentrated again under reduced pressure. Ethyl acetate was added to the residue and the solid was collected by filtration and dried under reduced pressure to give the title compound (663 mg) as a solid powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethanol (50 mL)
  2. additionwas added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. filtrationthe solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b25460c3526e400fbf67d72aa76ce5f2
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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