Hydrochloric Acid → HCID 57597312, compound

HRID 1926041Notes

Reaction equation

HRID 1926041 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[NH:26][C:25](/[CH:27]=[CH:28]/[CH2:29][NH:30]C(=O)OC(C)(C)C)=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.[OH-].[Na+]>O1CCCC1>[NH2:30][CH2:29]/[CH:28]=[CH:27]/[C:25]1[NH:26][C:19]2[C:18]([NH:17][C:4]3[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=4)=[C:2]([Cl:1])[CH:3]=3)=[N:23][CH:22]=[N:21][C:20]=2[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86615764HCID 86615764, compound

Product 1

HCID 57597312HCID 57597312, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl) oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-6-yl]prop-2-enylcarbamate (150 mg) in tetrahydrofuran (6.0 mL) was added 2N hydrochloric acid (3.0 mL) at room temperature and the mixture was stirred at 60° C. for 2 hrs. 1N Aqueous sodium hydroxide solution was added to alkalize the reaction system. After extraction with chloroform, the organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resultant crystals were collected by filtration. The crystals were washed with diisopropyl ether to give the title compound (104 mg) as pale-brown powder crystals.

Workup

  1. extractionAfter extraction with chloroform
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe resultant crystals were collected by filtration
  5. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-38bf54bb6a6d4aa58d65edc710496d6e
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

Loading…