HCID 86626257, compound → HCID 67520406, compound

HRID 1926154Notes

Reaction equation

HRID 1926154 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][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=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][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=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 86626257HCID 86626257, compound

Product 1

HCID 67520406HCID 67520406, compoundYield 410.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl [2-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-5H-pyrrolo[3,2-d]pyrimidin-5-yl)ethyl]carbamate (790 mg) was dissolved in tetrahydrofuran (24 mL)/2N hydrochloric acid (12 mL), and the mixture was stirred at 60° C. for 16 hrs. The reaction mixture was concentrated under reduced pressure, ethanol (30 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 (826 mg) as a solid powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethanol (30 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-99a0fa0c7b6e40718aa5b5d49b08cbe3
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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