N-methyl-2-pyrrolidone → 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3,5-difluoro-N-methyl-benzamide

HRID 1687645Notes

Reaction equation

HRID 1687645 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].CN1C(=O)CCC1.CCN(C(C)C)C(C)C.[Cl:30][C:31]1[N:36]=[C:35](Cl)[C:34]([Cl:38])=[CH:33][N:32]=1>>[Cl:30][C:31]1[N:36]=[C:35]([NH:1][C:2]2[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][C:3]=2[C:4]([NH:6][CH3:7])=[O:5])[C:34]([Cl:38])=[CH:33][N:32]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 672646322-Amino-3,5-difluoro-N-methyl-benzamide

Product 1

HCID 866339982-(2,5-Dichloro-pyrimidin-4-ylamino)-3,5-difluoro-N-methyl-benzamide

Conditions

Temperature
100 °C

Procedure

To a solution of 2-Amino-3,5-difluoro-N-methyl-benzamide (1.099 g, 0.006 mol) and NMP (6 mL, 0.06 mol) was added DIEA (1.23 mL, 7.8 mmol) followed by 2,4,5-Trichloro-pyrimidine (0.812 mL, 7.1 mmol) and the reaction mixture was heated at 100° C. for 16 h. Title compound isolated as an off-white solid (1.10 g, 56%), MP=220-221, HPLC purity=95%, LCMS=333.38 (M+H), 1H-NMR (CDCl3, 400 MHz) δ 8.94 (s, 1H), 8.22 (s, 1H), 7.12-7.06 (m, 2H), 6.17 (s, 1H), 2.99 (s, 3H).

Sources & evidence

ORD record
ord-d703032de2034bd282f0e089482cee7e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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