Methylamine → HCID 22177258, compound

HRID 1797163Notes

Reaction equation

HRID 1797163 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:27][CH:28]=O)[C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:30][NH2:31]>ClCCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH2:27][CH2:28][NH:31][CH3:30])[C:16]([NH:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)=[O:17])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22177238HCID 22177238, compound

Product 1

HCID 22177258HCID 22177258, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-(3′-cyano-biphenyl-4-yl)-N-(3,5-dichloro-phenyl)-4oxo-butyramide (300 mg, 0.71 mmol) and MeNH2 (2M in THF, 1.77 mL, 3.54 mmol, 5 eq) in 1,2-dichloroethane (3.5 mL) was stirred at r.t. for 1 h and then Na(AcO)3BH (299 mg, 1.4 mmol, 2 eq) was added. The reaction mixture was stirred at r.t. for 16 h. The mixture was then partitioned between EtOAc (20 mL) and 10% NaHCO3 (10 mL) and the organic phase separated. The organic phase was washed with 10% NaHCO3 (10 mL×2), saturated brine (10 mL), dried (Na2SO4), and concentrated. Chromatography on silica gel (Et3N/MeOH/CH2Cl2 1:10:90) gave 56.5 mg (18%) of the title compound as a yellowish gum. 1H NMR (300 MHz, CDCl3): δ 7.89 (m, 2H), 7.72 (m, 1H), 7.61 (m, 7H), 7.14 (t, 1H), 4.04 (dd, 1H), 2.85 (t, 2H), 2.59 (s, 3H), 2.50 (m, 1H), 2.16 (m, 1H). MS(ESI): 438.0 (M+1), 440.0 (M+3).

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 16 h
  2. customThe mixture was then partitioned between EtOAc (20 mL) and 10% NaHCO3 (10 mL)
  3. customthe organic phase separated
  4. washThe organic phase was washed with 10% NaHCO3 (10 mL×2), saturated brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee936a03377f4b3cb096e513f296fffa
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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