Triethylamine → HCID 178452655, compound

HRID 2220139Notes

Reaction equation

HRID 2220139 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]1[N:26]2[N:27]=[CH:28][CH:29]=[C:25]2[C:24]([C:30]#[N:31])=[C:23](O)[CH:22]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[NH2:73][C@H:74]1[CH2:79][CH2:78][C@H:77]([NH2:80])[CH2:76][CH2:75]1>O1CCOCC1.C(OCC)(=O)C>[NH2:73][C@H:74]1[CH2:79][CH2:78][C@H:77]([NH:80][C:23]2[CH:22]=[C:21]([N:8]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][CH:10]=3)[C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[N:26]3[N:27]=[CH:28][CH:29]=[C:25]3[C:24]=2[C:30]#[N:31])[CH2:76][CH2:75]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 178452656HCID 178452656, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178452655HCID 178452655, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(tert-Butoxy)-N-[4-cyano-5-hydroxy(pyrazolo[1,5-a]pyridin-7-yl)]7-N-(4-biphenylyl)carboxamide (40) (27 mg) was dissolved in 1,4-dioxane (600 μL)and to this solution were added triethylamine (22 μL) and benzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate (36 mg). This mixture was stirred at room temperature for 10 min. Trans-1,4-Diaminocyclohexane (145 mg) was added and the mixture was further stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with 1 mol/L aqueous sodium hydroxide solution, dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified with thin layer silica gel column chromatography (ethyl acetate/2 mol/L methanolic ammonia solution=5/1) to obtain the title compound (46).

Workup

  1. stirringthe mixture was further stirred at room temperature for 4 h
  2. washthe organic layer was washed with 1 mol/L aqueous sodium hydroxide solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified with thin layer silica gel column chromatography (ethyl acetate/2 mol/L methanolic ammonia solution=5/1)

Sources & evidence

ORD record
ord-3891723de26b4260b32a5574ddfd2ef9
Source dataset
uspto-grants-2008_08
Patent number
US07417053B2

Reaction notes

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