3-Aminopyridine → HCID 58063619, compound

HRID 2035713Notes

Reaction equation

HRID 2035713 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[F:8][C:9]1[C:14]2[CH2:15][CH2:16][CH:17]([N:26]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34](I)=[C:33]([O:38][CH3:39])[CH:32]=4)[N:28]=[N:27]3)[C:18](=[O:25])[N:19]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C(O)(CC)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:8][C:9]1[C:14]2[CH2:15][CH2:16][CH:17]([N:26]3[CH:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([NH:7][C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[C:33]([O:38][CH3:39])[CH:32]=4)[N:28]=[N:27]3)[C:18](=[O:25])[N:19]([CH2:20][C:21]([F:22])([F:23])[F:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666829706-Fluoro-3-[4-(4-iodo-3-methoxy-phenyl)-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoro-ethyl)-1,3,4,5-tetrahydro-1-benzazepin-2-one

Product 1

HCID 58063619HCID 58063619, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 64052-Methyl-2-butanolSolvent

Procedure

A suspension of pyridin-3-amine (5.08 mg, 0.054 mmol), 6-fluoro-3-[4-(4-iodo-3-methoxyphenyl)-1H-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (30 mg, 0.054 mmol), potassium carbonate (8.14 mg, 0.059 mmol), X-Phos (12.76 mg, 0.027 mmol), and tris(dibenzylideneacetone)dipalladium (9.81 mg, 0.011 mmol) were combined in a μwave vial and dissolved in t-amyl alcohol (1071 μl). The reaction was microwaved at 130° C. for 20 min. The reaction mixture was filtered, and the solvent was removed 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-methoxy-4-(pyridin-3-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 microwaved at 130° C. for 20 min
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customAnalytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18)
  5. washeluting with acetonitrile/water+0.05% Formic Acid

Sources & evidence

ORD record
ord-4bb14abf63da4b258cb538643098a04b
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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