Ammonium Chloride → HCID 59667329, compound

HRID 1671522Notes

Reaction equation

HRID 1671522 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:19]=3[CH3:27])[C:8]=2[C:9](Cl)=[N:10][CH:11]=1)=[O:5])[CH3:2].[NH4+].[Cl-]>O1CCOCC1.C1COCC1.CN(C=O)C.O.C(OCC)(=O)C.[Zn]>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:19]=3[CH3:27])[C:8]=2[CH:9]=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

9

Reactant 2

HCID 25517Ammonium ChlorideHCID 596673284-Chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

Product 1

HCID 59667329HCID 59667329, compound

Reagents, catalysts & solvents 6

HCID 23994ZincCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-chloro-3-(2-methyl-5-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (815.2 mg, 2.00 mmol) (from Example 22 supra) in 1,4-dioxane (40 mL), THF (20 mL) and DMF (20 mL) was added NH4Cl (1.59 mg, 29.6 mmol) in water (12 mL). Zinc powder (948 mg, 14.5 mmol) was then added in several portions and the reaction was stirred at room temperature for a total of 4 hours. The resulting mixture was diluted with ethyl acetate (800 mL), washed with water (100 mL) and then brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 95/5) to give 3-(5-amino-2-methyl-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 584 mg, 85%).

Workup

  1. washwashed with water (100 mL)
  2. dry with materialbrine (100 mL), dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (CH2Cl2/MeOH, 98/2 to 95/5)

Sources & evidence

ORD record
ord-e7278d025e994bfb9288188aee22bb02
Source dataset
uspto-grants-2011_08
Patent number
US07994321B2

Reaction notes

Loading…