Hydrochloric Acid → 1-{2-[3-(3-chloro-2-hydroxy-propylamino)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one

HRID 1677501Notes

Reaction equation

HRID 1677501 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:7]=[C:8]([C:12]3[N:13]=[C:14]4[C:20]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]4=[N:16][CH:17]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:3]1.[ClH:35]>CO>[Cl:35][CH2:3][CH:2]([OH:1])[CH2:5][NH:4][C:6]1[CH:7]=[C:8]([C:12]2[N:13]=[C:14]3[C:20]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595409881-[2-[3-(3-Hydroxy-azetidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one

Product 1

HCID 595407171-{2-[3-(3-chloro-2-hydroxy-propylamino)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-oneYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 1-[2-[3-(3-hydroxy-azetidin-1-yl)-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (36 mg, 0.075 mmol), in MeOH (1 ml), was treated with 18.5% HCl aq (1.75 ml). The reaction mixture was capped and heated to 90° C. for 1.5 hours. The reaction mixture was concentrated to dryness, and the resulting residue was taken up in 10 ml of EtOAc and 5 ml of sat. NaHCO3 aq. The reaction mixture was allowed to stir for 15 minutes and then extracted into EtOAc. The organic layers were collected, dried over MgSO4, filtered, concentrated. Silica gel chromatography using 0-10% MeOH in EtOAc as eluant gave 10 mg (35%) of 1-{2-[3-(3-chloro-2-hydroxy-propylamino)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one as a yellow solid. M+H=387.

Workup

  1. customThe reaction mixture was capped
  2. concentrationThe reaction mixture was concentrated to dryness
  3. extractionextracted into EtOAc
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45493ad4576f4f3197a7a2486da09dac
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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