Hydrochloric Acid → HCID 57597340, compound

HRID 1925955Notes

Reaction equation

HRID 1925955 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:18]3[NH:25][C:24]([C:26]4[CH:27]=[C:28]([CH:38]=[CH:39][CH:40]=4)[CH2:29][NH:30]C(=O)OC(C)(C)C)=[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][C:12]([CH3:15])=[CH:13][CH:14]=1.Cl.[OH-].[Na+]>O1CCCC1>[NH2:30][CH2:29][C:28]1[CH:27]=[C:26]([C:24]2[NH:25][C:18]3[C:17]([NH:16][C:4]4[CH:5]=[CH:6][C:7]([O:8][C:9]5[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=5)=[C:2]([CH3:1])[CH:3]=4)=[N:22][CH:21]=[N:20][C:19]=3[CH:23]=2)[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67520674HCID 67520674, compound

Product 1

HCID 57597340HCID 57597340, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl 3-[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]benzylcarbamate (230 mg) was suspended in tetrahydrofuran (2.3 mL), 2N hydrochloric acid (2.3 mL) was added, and the mixture was stirred with heating at 60° C. for 3 hrs. After cooling to room temperature, 1N aqueous sodium hydroxide solution (4.6 mL) was added, and the mixture was stirred at room temperature for 5 min. The solvent was removed by decantation, and the residue was dissolved in tetrahydrofuran (30 mL), dried over potassium carbonate, and concentrated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration and dried under reduced pressure to give the title compound (164 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred at room temperature for 5 min
  3. customThe solvent was removed by decantation
  4. dissolutionthe residue was dissolved in tetrahydrofuran (30 mL)
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with diisopropyl ether
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-493f78fe16774ef79fa5742a56538119
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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