Acetic Acid → HCID 131729942, compound

HRID 2384946Notes

Reaction equation

HRID 2384946 reaction equation
[C:1](O)(=O)C.C=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:38][C:17]3[C:18](=[O:37])[N:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([CH:30]5[CH2:34][CH2:33][NH:32][CH2:31]5)=[O:29])=[C:24]([O:35][CH3:36])[CH:23]=4)[CH:20]=[CH:21][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.CCOCC>CO.C(Cl)Cl>[ClH:7].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:38][C:17]3[C:18](=[O:37])[N:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([CH:30]5[CH2:34][CH2:33][N:32]([CH3:1])[CH2:31]5)=[O:29])=[C:24]([O:35][CH3:36])[CH:23]=4)[CH:20]=[CH:21][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 10953452Ether hydrochlorideHCID 57649516HCID 57649516, compound

Product 1

HCID 131729942HCID 131729942, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Add acetic acid (1.50 g, 2.48 mmol) and formaldehyde (0.20 g, 2.48 mmol, 37% aqueous solution) to a solution of 2-(4-chloro-phenyl)-6-[3-methoxy-4-(pyrrolidine-3-carbonyl)-phenyl]-6H-thieno[2,3-c]pyridin-7-one, trifluoro-acetic acid (0.36 g, 0.62 mmol) in methanol (31 mL). Stir the mixture at RT for 15 min, then add sodium triacetoxyborohydride (0.55 g, 2.48 mmol), and continue to stir the mixture at RT for 2 h. Dilute the mixture with CH2Cl2 (200 mL), wash with saturated NaHCO3, and back extract the aqueous with CH2Cl2 (100 mL). Wash the combined organic phases with water (100 mL), dry over Na2SO4, filter, and concentrate. Purify the crude material by filtering with Et2O (100 mL) and water (50 mL). To prepare the HCl salt dissolve the solid in CH2Cl2, and add 1 eq 1M HCl/ether. Allow the solution to stir for 15 min, and concentrate to give 0.16 g (50%) of the title compound. LC-MS/ES m/z (35Cl) 479.0 [M+H]+.

Workup

  1. stirringto stir the mixture at RT for 2 h
  2. washwash with saturated NaHCO3
  3. extractionback extract the aqueous with CH2Cl2 (100 mL)
  4. washWash the combined organic phases with water (100 mL)
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material
  9. filtrationby filtering with Et2O (100 mL) and water (50 mL)
  10. customTo prepare the HCl salt
  11. stirringto stir for 15 min
  12. concentrationconcentrate

Sources & evidence

ORD record
ord-a531bc9249554b4e9a10884dc127ecd3
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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