Trifluoroacetic acid → HCID 86664554, compound

HRID 513300Notes

Reaction equation

HRID 513300 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12]3[CH:20]=[C:19]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=4[F:30])[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:7][CH:6]=2)[CH2:2]1.CCN(C(C)C)C(C)C.[C:40](O)(C(F)(F)F)=[O:41]>CN(C=O)C>[F:30][C:24]1[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][NH:21][C:19]1[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([CH:3]3[CH2:4][N:1]([CH:40]=[O:41])[CH2:2]3)=[CH:6][CH:7]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 67501654HCID 67501654, compound

Product 1

HCID 86664554HCID 86664554, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 6-(4-(azetidin-3-yl)phenylamino)-4-(2,3-difluorobenzylamino)nicotinamide (Example 212) (35 mg, 0.08 mmol) was stirred in 4 mL DMF with DIEA (300 μL) at 120° C. in a sealed tube for three days. The mixture was acidified with 0.5 mL TFA and subjected to reverse phase preparative HPLC to isolate the title compound (11 mg). MS found for C23H21F2N5O2 as (M+H)+ 438.4. UV: λ=259 nm. 1H NMR: (CD3OD) δ 8.17 (1H, s), 8.02 (1H, s), 7.44 (2H, dt, J=8.0; 1.6 Hz), 7.24 (1H, m), 7.17 (2H, dt, J=8.4; 1.6 Hz), 7.14 (1H, m), 7.11 (1H, m), 5.82 (1H, s), 4.68 (1H, t, J=8.0 Hz), 4.56 (2H, s), 4.46 (1H, m), 4.27 (1H, m), 4.05 (2H, m) ppm.

Sources & evidence

ORD record
ord-555dc3c16874406db0123c83b46cfcba
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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