Tert-Butylamine → N-(4-(2,3-difluorophenylamino)pyridin-3-yl)-2-(tert-butylamino)pyridine-3-carboxamide

HRID 253972Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][C:17]([C:19]1[C:20](F)=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18].[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>CN1C(=O)CCC1.O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][C:17]([C:19]1[C:20]([NH:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-(4-(2,3-difluorophenylamino)pyridin-3-yl)-2-fluoropyridine-3-carboxamide (4.0 g, 11.6 mmol) in NMP (30 mL) was added t-butylamine (15.0 mL, 145.3 mmol) at RT. The reaction mixture was slowly heated to 100° C. and stirred at this temperature for 48 hr. The reaction mixture was diluted with water (150 mL) and extracted with EtOAc (3×200 mL). The combined organics were washed with water (4×100 mL), brine solution (100 mL), and dried (Na2SO4). Filtration and evaporation of solvent in vacuo gave N-(4-(2,3-difluorophenylamino)pyridin-3-yl)-2-(tert-butylamino)pyridine-3-carboxamide (4.1 g, 89% yield), which was used as is in subsequent reactions; LC-MS: 398.3 (M+H).

Workup

extractionextracted with EtOAc (3×200 mL)
washThe combined organics were washed with water (4×100 mL), brine solution (100 mL)
dry with materialdried (Na2SO4)
filtrationFiltration and evaporation of solvent in vacuo

Sources & evidence

ORD record: ord-3158a4c86e97489490d5e2b751e226b8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872031B2

Reaction notes

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