Trifluoroacetic acid → HCID 67502559, compound
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.[C:33]([CH2:35][C:36](O)=[O:37])#[N:34].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(O)(C(F)(F)F)=O>CN1C(=O)CCC1>[C:33]([CH2:35][C:36]([N:25]1[CH2:24][CH2:23][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:8]3[CH:7]=[C:6]([NH:5][CH2:4][C:3]4[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:2]=4[F:1])[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=3)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)=[O:37])#[N:34]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The mixture of 4-(2,3-difluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 209) (90 mg, 0.19 mmol), cyanoacetic acid (81 mg, 0.95 mmol), DIEA (330 μL, 1.9 mmol) in 4 mL NMP was stirred at RT. To it was added BOP (360 mg, 0.95 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 (81 mg). MS found for C27H26F2N6O2 as (M+H)+ 505.4. UV: λ=259 nm. 1H NMR: (CD3OD) δ 8.05 (1H, s), 7.24 (2H, d, J=8.4 Hz), 7.15 (1H, m), 7.06 (1H, m), 7.04-6.97 (3H, m), 5.71 (1H, s), 4.56 (1H, m), 4.46 (2H, s), 3.91-3.77 (3H, m), 3.16 (1H, m), 2.83-2.69 (2H, m), 1.84 (2H, m), 1.60 (2H, m) ppm.
Workup
- stirringThe mixture was stirred at RT for overnight
Sources & evidence
- ORD record
- ord-f4097bcf37c44c3192e97453fa192ee0
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102625B2
Reaction notes
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