Trifluoroacetic acid → HCID 86664553, compound

HRID 513299Notes

Reaction equation

HRID 513299 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:29]([F:32])=[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.[C:42](O)(C(F)(F)F)=[O:43]>CN(C=O)C>[F:1][C:2]1[CH:31]=[CH:30][C:29]([F:32])=[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[CH2:23][CH2:24][N:25]([CH:42]=[O:43])[CH2:26][CH2:27]3)=[CH:18][CH:17]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 67502109HCID 67502109, compound

Product 1

HCID 86664553HCID 86664553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4-(2,5-difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 214) (70 mg, 0.15 mmol) was stirred in 4 mL DMF with DIEA (300 μL) at 120° C. in a sealed tube for two days. The mixture was acidified with 0.5 mL TFA and subjected to reverse phase preparative HPLC to isolate the title compound (46 mg). MS found for C25H25F2N5O2 as (M+H)+ 466.4. UV: λ=259 nm. 1H NMR: (CD3OD) δ 8.05 (1H, s), 7.97 (1H, s), 7.25 (2H, dt, J=8.8; 2.0 Hz), 7.08-6.98 (4H, m), 6.94 (1H, m), 5.74 (1H, s), 4.41 (2H, s), 4.38 (1H, m), 3.77 (1H, m), 3.17 (1H, m), 2.83 (1H, m), 2.72 (1H, m), 1.85 (2H, m), 1.53 (2H, m) ppm.

Sources & evidence

ORD record
ord-a0f22ccece674a0f9d89fc2ccff2c8b2
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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