4-Aminopyridine → HCID 58063524, compound

HRID 2035726Notes

Reaction equation

HRID 2035726 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH:13]3[CH2:19][CH2:18][C:17]4[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:14]3=[O:30])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[N:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:24][C:20]1[C:17]2[CH2:18][CH2:19][CH:13]([N:11]3[CH:12]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:37][C:34]5[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=5)[CH:3]=4)[N:9]=[N:10]3)[C:14](=[O:30])[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:16]=2[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66683136HCID 66683136, compound

Product 1

HCID 58063524HCID 58063524, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-[4-(3-Chlorophenyl)-1H-1,2,3-triazol-1-yl]-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (20 mg, 0.046 mmol), pyridin-4-amine 6.39 mg, 0.068 mmol), palladium(II) acetate (2.047 mg, 9.12 μmol), Xantphos (7.91 mg, 0.014 mmol), and cesium carbonate (44.6 mg, 0.137 mmol) were combined and dissolved in dioxane (912 μl). The reaction was irradiated in the microwave at 180° C. for 15 minutes. The completed reaction was filtered and concentrated in vacuo. Analytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% formic acid. Lyophilisation afforded 6-fluoro-3-{4-[3-(pyridin-4-ylamino)phenyl]-1H-1,2,3-triazol-1-yl}-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one.

Workup

  1. customThe reaction was irradiated in the microwave at 180° C. for 15 minutes
  2. customThe completed reaction
  3. filtrationwas filtered
  4. concentrationconcentrated in vacuo
  5. customAnalytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18)
  6. washeluting with acetonitrile/water+0.05% formic acid

Sources & evidence

ORD record
ord-d56a2c0455454ed5814558f2135ae39e
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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