Hydrochloric Acid → HCID 71059798, compound

HRID 423418Notes

Reaction equation

HRID 423418 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=4)[S:19][C:13]=3[C:12]2=[O:27])=CN=1)=[O:4].[N:28]1([CH2:33][CH2:34][NH2:35])[CH2:32][CH2:31][CH2:30][CH2:29]1.[Al](C)(C)[CH3:37].Cl.[CH3:41][CH2:42][OH:43]>C1(C)C=CC=CC=1.C(Cl)Cl>[ClH:26].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]2[S:19][C:13]3[C:12](=[O:27])[N:11]([C:8]4[CH:9]=[CH:10][C:5]([C:3]([NH:35][CH2:34][CH2:33][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:4])=[C:42]([O:43][CH3:37])[CH:41]=4)[CH2:16][CH2:15][C:14]=3[CH:17]=2)=[CH:21][CH:22]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13441-PyrrolidineethanamineHCID 16682925TrimethylaluminumHCID 66673662HCID 66673662, compound

Product 1

HCID 71059798HCID 71059798, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Mix 5-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-pyridine-2-carboxylic acid methyl ester (0.099 g, 0.25 mmol) with 2-pyrrolidin-1-yl-ethylamine (34 mg) in toluene (5 mL). Add Al(CH3)3 (130 μL, 0.26 mmol) and stir the mixture at 60° C. overnight. Cool to 0° C. and quench with water (5 mL). Dilute with EtOAc (20 mL) and filter off the insoluble material. Dilute the filtrate with EtOAc (50 mL), wash with saturated NaHCO3 (2×30 mL), dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography, eluting with 10% CH3OH (2N NH3)/CH2Cl2 to give 0.058 g. Dissolve the material in CH2Cl2 (5 mL) and treat with 1.0 M HCl in EtOH (118 μL). Stir at RT for 5 min and concentrate to give 0.051 g, (39%) of the title compound. LC-MS/ES (35Cl) 481.2 [M+H]+.

Workup

  1. customquench with water (5 mL)
  2. additionDilute with EtOAc (20 mL)
  3. filtrationfilter off the insoluble material
  4. additionDilute the filtrate with EtOAc (50 mL)
  5. washwash with saturated NaHCO3 (2×30 mL)
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by chromatography
  10. washeluting with 10% CH3OH (2N NH3)/CH2Cl2
  11. customto give 0.058 g
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-931f4e2dbde14cf493b34df27ed49cd7
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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