Trifluoroacetic acid → HCID 67502230, compound

HRID 513308Notes

Reaction equation

HRID 513308 reaction equation
[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:7]=1.CCN(C(C)C)C(C)C.F[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=1.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1>[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:23][CH2:24][N:25]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=4)[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 97462-FluoropyridineHCID 81531DiisopropylethylamineHCID 675004384-(2,3-Difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide

Product 1

HCID 67502230HCID 67502230, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
125 °C

Procedure

The mixture of 4-(2,3-difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 209) (55 mg, 0.11 mmol), DIEA (0.1 mL, 0.55 mmol), 2-fluoropyridine (110 mg, 1.10 mmol) in 3 mL NMP was stirred in a sealed tube at 125° C. for 1 day. It was acidified with TFA and subjected to reverse phase preparative HPLC to isolate the title compound. MS found for C29H28F2N6O as (M+H)+ 515.4. UV: λ=249, 306 nm. 1H NMR: (CD3OD) δ 8.17 (1H, s), 8.00-7.94 (2H, m), 7.39 (1H, d, J=9.2 Hz), 7.36 (2H, dt, J=8.0; 2.0 Hz), 7.25 (1H, m), 7.18 (1H, m), 7.14-7.07 (3H, m), 6.94 (1H, t, J=7.2 Hz), 5.79 (1H, s), 4.55 (2H, s), 4.36 (2H, m), 3.38 (2H, m), 3.03 (1H, m), 2.08 (2H, m), 1.87 (2H, m) ppm.

Sources & evidence

ORD record
ord-a64eda0dbd924cceb954af586c936b3c
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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