2-Amino-4-methylpyridine → HCID 44178123, compound

HRID 1716501Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[C:15](=[O:20])[CH2:14]3)=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([C:11]2[S:12][C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=4)[N:7]=3)=[CH:9][N:10]=2)[CH2:14][C:15]1=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

4-[5-(6-bromopyridin-2-yl)thiazol-2-yl]-1-methylpiperazin-2-one obtained in Step 5 (188 mg, 0.53 mmol) was dissolved in toluene (5 ml), and after 2-amino-4-methylpyridine (58 mg, 0.53 mmol) was added, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (66 mg, 0.11 mmol), palladium acetate (18 mg, 0.08 mmol) and cesium carbonate (260 mg, 0.80 mmol) were added and the mixture was stirred overnight at 100° C. Water was added to the reaction solution and extracted with ethyl acetate and the organic layer was washed with a saturated saline solution. The organic layer was dried over sodium sulfate and after vacuum concentration, the residue was washed with methanol and the title compound (77 mg, 38%) was obtained.

Workup

extractionextracted with ethyl acetate
washthe organic layer was washed with a saturated saline solution
dry with materialThe organic layer was dried over sodium sulfate
concentrationafter vacuum concentration
washthe residue was washed with methanol

Sources & evidence

ORD record: ord-1a3a0c687a38470db48c8c096f4b6e71
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803801B2

Reaction notes

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