Dimethylformamide → HCID 89544887, compound

HRID 2283394Notes

Reaction equation

HRID 2283394 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([C:21]2[CH:26]=[N:25][C:24](Cl)=[CH:23][N:22]=2)=[O:20])[C:13]=1[F:28])[CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1.C(N(CC)CC)C.CN(C)C=O>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([C:21]2[CH:26]=[N:25][C:24]([NH:37][CH2:36][C:35]3[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)=[CH:23][N:22]=2)=[O:20])[C:13]=1[F:28])[CH:9]1[CH2:10][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 89545051HCID 89545051, compound

Product 1

HCID 89544887HCID 89544887, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Step 2 {(R)-[4-Chloro-3-(5-chloro-pyrazine-2-carbonyl)-2-fluoro-phenyl]-cyclopropyl-methyl}-carbamic acid tert-butyl ester (709 mg, 1.61 mmol), 4-methoxybenzylamine (0.232 ml, 1.77 mmol), triethylamine (0.448 ml, 3.22 mmol) and dimethylformamide (5 ml) was heated to 80 deg C for 3 hours. The reaction was allowed to cool, ethyl acetate was added, and the mixture was washed with 10% aqueous lithium chloride solution and brine. The organic liquors were dried (MgSO4) and concentrated. The residue was purified by column chromatography eluting with 10-50% ethyl acetate/petroleum ether furnishing ((R)-{4-Chloro-2-fluoro-3-[5-(4-methoxy-benzylamino)-pyrazine-2-carbonyl]-phenyl}-cyclopropyl-methyl)-carbamic acid tert-butyl ester (512 mg) as a yellow oil. [M+H]+ 541

Workup

  1. temperatureto cool
  2. washthe mixture was washed with 10% aqueous lithium chloride solution and brine
  3. dry with materialThe organic liquors were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with 10-50% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-afab2943eee94c2a8a5d5d0729d458d2
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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