Acetic Acid → HCID 59004666, compound

HRID 1668496Notes

Reaction equation

HRID 1668496 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH2:18][CH2:17][C:16](=O)[CH2:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC(O)=O.Cl.[CH3:25][NH2:26].[OH-].[Na+]>ClCCCl>[CH3:25][NH:26][CH:16]1[CH2:17][CH2:18][C:13]([C:8]2[C:7]3[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[NH:10][CH:9]=2)=[CH:14][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 6364545Methylamine hydrochlorideHCID 59004602HCID 59004602, compound

Product 1

HCID 59004666HCID 59004666, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of compound 119 (0.5 g, 1.951 mmol) in 1,2-dichloroethane (10 mL) was treated with AcOH (0.11 mL, 1.951 mmol), methylamine hydrochloride (0.13 g, 1.951 mmol), NaBH(OAC)3 (0.62 g, 2.926 mmol) at room temperature and stirred for over night (16 h). The reaction was basified with 2 N NaOH (25 mL) and product was extracted into ethyl acetate (2×25 mL). The combined ethyl acetate layer washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 120 (0.47 g, 89%) as a solid. mp 170-172° C.; 1H NMR (DMSO-d6) δ 1.37-1.50 (m, 1H), 1.90-1.99 (m, 2H), 2.33 (s, 3H), 2.43-2.64 (m, 4H), 6.14 (brs, 1H), 7.80 (s, 1H), 7.86-7.96 (m, 2H), 8.30 (d, 1H, J=2.1 Hz); ESI-MS (m/z, %): 272 (MH+, 100), 241 (43).

Workup

  1. extractionwas extracted into ethyl acetate (2×25 mL)
  2. washThe combined ethyl acetate layer washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-c7ccbba9755044a193692f3844ac5d44
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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