Hydrochloric Acid → HCID 10068101, compound

HRID 2219000Notes

Reaction equation

HRID 2219000 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:52].Cl.Cl>C(Cl)Cl.CCOCC.CO.C(O)(=O)C>[ClH:52].[ClH:52].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 451567664-[(4-Methyl-1-piperazinyl)carbonyl]benzaldehyde

Product 1

HCID 10068101HCID 10068101, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 16 (60 mg) and morpholine (0.025 mL) in DCM (5 mL) was added acetic acid (0.015 mL) and sodium triacetoxyborohydride (83 mg). After 16 h the reaction was treated with 1 N NaOH (10 mL) and extracted with DCM (3×20 mL). Organic layers were dried (Na2SO4), concentrated under reduced pressure, and chromatographed on silica gel (4% 2 M methanolic ammonia/DCM) to give the free base product. This material was converted into the dihydrochloride using methanol and 2 M HCl in ether to form a white solid (35 mg).

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialOrganic layers were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed on silica gel (4% 2 M methanolic ammonia/DCM)
  5. customto give the free base product

Sources & evidence

ORD record
ord-6a76931fad374c899cf1e39adb2683f6
Source dataset
uspto-grants-2008_08
Patent number
US07414047B2

Reaction notes

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