Sodium Bicarbonate → {2-Chloro-4-[(2-{2-[(2,3-dihydroxypropyl)amino]ethyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

HRID 1797301Notes

Reaction equation

HRID 1797301 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][NH:17][CH2:18][CH:19]2[CH2:23][O:22]C(C)(C)[O:20]2)[CH:5]=[CH:4][C:3]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:27].C([O-])(O)=O.[Na+]>Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][CH2:16][NH:17][CH2:18][CH:19]([OH:20])[CH2:23][OH:22])[CH:5]=[CH:4][C:3]=1[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])=[O:27]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22174521HCID 22174521, compound

Product 1

HCID 10138068{2-Chloro-4-[(2-{2-[(2,3-dihydroxypropyl)amino]ethyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

Compound 144 was dissolved in 1M HCl/THF 1:1 (1.2 mL) and the mixture was stirred for 18 h at RT. The reaction mixture was poured into 10% aqueous NaHCO3 (10 mL) and the aqueous phase was extracted with EtOAc (3×10 mL). The combined organic phases were dried (MgSO4), filtered and evaporated in vacuo. This afforded the title compound as a yellow oil.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-70b91501c1084998b9bbb3db5e1ce3b7
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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