Potassium Carbonate → Hydroxide

HRID 1667692Notes

Reaction equation

HRID 1667692 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([CH:25]=O)[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][NH:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl-].[NH4+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[OH-:14].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:16]3[C:20]4[CH:21]=[C:22]([CH2:25][N:31]([CH2:30][CH2:29][N:28]([CH3:33])[CH3:27])[CH3:32])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 866428104-(3-Chloro-phenyl)-2-(6-formyl-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide

Product 2

HCID 961HydroxideHCID 468349014-(3-Chloro-phenyl)-2-(6-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-benzoimidazol-1yl)-thiazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.065 g (0.17 mmole) of 4-(3-chloro-phenyl)-2-(6-formyl-benzoimidazol-1-yl)-thiazole-5-carboxylic acid amide (I.2a), 0.060 mL of N,N,N′-trimethyl-ethane-1,2-diamine, 0.10 g of sodium triacetoxyborohydride and 5 mL of dichloromethane was stirred at room temperature for 6 hours, after which 1 mL of saturated aqueous ammonium chloride solution was added. The mixture was stirred at room temperature for 30 minutes, made basic by addition of saturated potassium carbonate solution and partitioned between 30 mL of dichloromethane and 30 mL of dilute potassium carbonate solution. The aqueous layer was extracted twice with 30 mL of dichloromethane. The combined dichloromethane layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane-ammonium:hydroxide (10:90:1) to give 0.041 g of 4-(3-chloro-phenyl)-2-(6-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-benzoimidazol-1yl)-thiazole-5-carboxylic acid amide (I.6) as a light pink solid. MH+/Z=469

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. custompartitioned between 30 mL of dichloromethane and 30 mL of dilute potassium carbonate solution
  3. extractionThe aqueous layer was extracted twice with 30 mL of dichloromethane
  4. washThe combined dichloromethane layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with methanol-dichloromethane-ammonium

Sources & evidence

ORD record
ord-d73ca706a4944916928bf7d31c01e88e
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

Loading…