Diisopropylethylamine → 6-chloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)pyridine-3-carboxamide

HRID 1526051Notes

Reaction equation

HRID 1526051 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][C:21]4[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=4)[CH:18]=3)[NH:13][N:12]=2)=[O:9])=[CH:6][CH:5]=[C:4]([Cl:29])[N:3]=1.CCN(C(C)C)C(C)C.[O:39]1[CH2:44][CH2:43][CH:42]([NH2:45])[CH2:41][CH2:40]1>O1CCOCC1.CCOC(C)=O>[Cl:29][C:4]1[N:3]=[C:2]([NH:45][CH:42]2[CH2:43][CH2:44][O:39][CH2:40][CH2:41]2)[C:7]([C:8]([NH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][C:21]4[CH:22]=[C:23]([F:28])[CH:24]=[C:25]([F:27])[CH:26]=4)[CH:18]=3)[NH:13][N:12]=2)=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 866476302,6-dichloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]pyridine-3-carboxamide

Product 1

HCID 866476316-chloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,6-dichloro-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]pyridine-3-carboxamide (80 mg, 0.18 mmol) in dioxane (1 mL) was heated at 100° C. for 24 hours in the presence of DIPEA (0.1 mL, 0.55 mmol) and tetrahydro-2H-pyran-4-amine. (28 mg, 0.28 mmol) Reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography on silica gel using DCM/EtOH 95:5 as the eluant, affording 57 mg of the title compound.

Workup

  1. custom(28 mg, 0.28 mmol) Reaction mixture
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d66f8e33fc4b49c0a8f0d432995d028d
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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