1,10-Phenanthroline → HCID 178454064, compound

HRID 1041905Notes

Reaction equation

HRID 1041905 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:12]=3)=[N:9][N:10]=2)[CH:7]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:46][C:47]([O:50][C:51]([NH:53][CH:54]1[CH2:59][CH2:58][CH:57]([OH:60])[CH2:56][CH2:55]1)=[O:52])([CH3:49])[CH3:48]>C1(C)C=CC=CC=1.CCOC(C)=O.[Cu]I>[C:47]([O:50][C:51](=[O:52])[NH:53][C@H:54]1[CH2:55][CH2:56][C@H:57]([O:60][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)[CH:12]=4)=[N:9][N:10]=3)[CH:7]=2)[CH2:58][CH2:59]1)([CH3:49])([CH3:46])[CH3:48]

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanolHCID 669775456-Iodo-3-[3-(2-morpholin-4-yl-ethoxy)-phenyl]-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 178454064HCID 178454064, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 1 step b (234 mg, 0.52 mmol), copper (I) iodide (9 mg, 0.052 mmol), 1,10-phenanthroline (19 mg, 0.104 mmol), cesium carbonate (335 mg, 1.04 mmol) and trans-4-boc-aminocyclohexanol (560 mg, 2.6 mmol) in toluene (3 mL) was heated at 110° C. for 72 h under an argon atmosphere. The suspension was cooled to RT, diluted with EtOAc (10 mL) and filtered through HiFlo. The filtrate was concentrated in vacuo and the residue purified by reverse phase preparative HPLC (Method 3) to afford the title compound (205 mg, 39%) as an off-white solid. LCMS (Method 2): Rt 2.53 min, m/z 538 [MH+].

Workup

  1. filtrationfiltered through HiFlo
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by reverse phase preparative HPLC (Method 3)

Sources & evidence

ORD record
ord-c00f5bfe70e341b997c8ca8b566c3676
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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