Trifluoroacetic acid → HCID 86664555, compound

HRID 513301Notes

Reaction equation

HRID 513301 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]=[C:27]([F:29])[CH:26]=[CH:25][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.C[C:32](N(C)C)=[O:33].C(O)(C(F)(F)F)=O>CN(C=O)C>[F:30][C:24]1[CH:25]=[CH:26][C:27]([F:29])=[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:32]=[O:33])[CH2:2]3)=[CH:6][CH:7]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31374DimethylacetamideHCID 67502757HCID 67502757, compound

Product 1

HCID 86664555HCID 86664555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 6-(4-(azetidin-3-yl)phenylamino)-4-(2,5-difluorobenzylamino)nicotinamide (Example 213) (35 mg, 0.08 mmol) was stirred in 4 mL DMF with DMA (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 (15 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), 7.21 (1H, m), 7.15-7.04 (3H, m), 5.85 (1H, s), 4.67 (1H, m), 4.51 (2H, s), 4.46 (1H, m), 4.27 (1H, m), 4.04 (2H, m) ppm.

Sources & evidence

ORD record
ord-9b7b73f0d09e432d89288e35f78b5566
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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