3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-[4-Methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]nicotinamide

HRID 1765237Notes

Reaction equation

HRID 1765237 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([CH:24]=1)[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:9]=1.Cl.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1>>[CH3:25][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=2)=[CH:24][C:6]=1[NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:9]=1

Participants

3

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 227324584-(5-Amino-2-methylanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine

Product 1

HCID 22732504N-[4-Methyl-3-(2-pyridin-4-yl-6-(trifluoromethyl)pyrimidin-4-ylamino)-phenyl]nicotinamide

Procedure

The title compound was prepared from a mixture of 4-(5-amino-2-methylanilino)-2-(4-pyridinyl)-6-(trifluoromethyl)pyrimidine (20 mg, 0.058 mmol) and nicotinoyl chloride hydrochloride (10 mg, 0.058 mmol) similar to Example 139 and isolated as a tan solid (13 mg, 47%). 1H NMR (DMSO-d6): 10.50 (s, 1H), 9.85 (s, 1H), 9.12 (d, J=1.5 Hz, 1H), 8.77 (dd, J=1.5, 4.5 Hz, 1H), 8.72 (d, J=5.7 Hz, 2H), 8.34–8.28 (m, 1H), 8.21 (bs, 1H), 8.16 (d, J=6.0 Hz, 2H), 7.60–7.53 (m, 2H), 7.34 (d, J=8.1 Hz, 1H), 7.14 (s, 1H), 2.25 (s, 3H).

Sources & evidence

ORD record
ord-669ca5612d9c4f3bbac43baefd7967f2
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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