Trifluoroacetic acid → HCID 67502054, compound

HRID 513312Notes

Reaction equation

HRID 513312 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[P-](F)(F)(F)(F)F.[N:49]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57]C=2N=N1.[C:69](O)([C:71](F)(F)F)=[O:70]>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:69](=[O:70])[CH2:71][N:49]4[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]4)[CH2:26][CH2:27]3)=[CH:20][CH:21]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 675004384-(2,3-Difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide

Product 1

HCID 67502054HCID 67502054, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of 4-(2,3-difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 209) (80 mg, 0.17 mmol), 4-morphonlineacetic acid (100 mg, 0.68 mmol), DIEA (240 μL, 1.36 mmol) in 4 mL NMP was stirred at RT. To it was added BOP (260 mg, 0.68 mmol). The mixture was stirred at RT for overnight. To it was added TFA (0.5 mL). The mixture was subjected to reverse phase preparative HPLC to isolate the title compound (70 mg). MS found for C31H36F2N6O2 as (M+H)+ 563.5. UV: λ=259 nm. 1H NMR: (CD3OD) δ 8.18 (1H, s), 7.34-7.11 (7H, m), 5.80 (1H, s), 4.55 (2H, s), 4.35-4.26 (4H, m), 3.83 (2H, m), 3.60 (2H, m), 3.05 (2H, m), 2.89 (1H, m), 1.95-1.57 (10H, m) ppm.

Workup

  1. stirringThe mixture was stirred at RT for overnight

Sources & evidence

ORD record
ord-1de118e970aa44fbb081c79dd9a0acd2
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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