Pyridine → HCID 178507781, compound

HRID 410115Notes

Reaction equation

HRID 410115 reaction equation
ClC(N(C)C)=C(C)C.[F:9][CH:10]([F:25])[O:11][C:12]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([NH2:24])=[CH:17][C:13]=1[C:14]([OH:16])=O.[F:26][C:27]([F:36])([F:35])[C@H:28]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]1.N1C=CC=CC=1>C(Cl)Cl.C1COCC1>[F:26][C:27]([F:35])([F:36])[C@H:28]1[CH2:29][CH2:30][C@H:31]([NH:34][C:14](=[O:16])[C:13]2[CH:17]=[C:18]([NH2:24])[C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:12]=2[O:11][CH:10]([F:9])[F:25])[CH2:32][CH2:33]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 667654082-(Difluoro-methoxy)-5-amino-4-nitro-benzoic acidHCID 178511531HCID 178511531, compound

Product 1

HCID 178507781HCID 178507781, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(1-Chloro-2-methyl-propenyl)-dimethylamine (102 μl) is added to a mixture of 2-(difluoro-methoxy)-5-amino-4-nitro-benzoic acid (175 mg, 0.705 mmol, prepared in analogy to WO2010/034797), 5 mL THF and 10 mL DCM and it is stirred for 5 h. Then trans-4-trifluoromethyl-cyclohexylamine (158 mg, 0.776 mmol) and pyridine (139 μL, 1.77 mmol) are added and it is stirred overnight. The solvent is removed i. vac., half-saturated aq. NaHCO3— solution is added and it is extracted with DCM. The organic layers are dried with Na2SO4, filtered, concentrated and purified via preparative HPLC (Method F).

Workup

  1. stirringit is stirred overnight
  2. customThe solvent is removed i
  3. addition, half-saturated aq. NaHCO3— solution is added
  4. extractionit is extracted with DCM
  5. dry with materialThe organic layers are dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via preparative HPLC (Method F)

Sources & evidence

ORD record
ord-81e8370de5a141069be77f4fe3b683ee
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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