Formamidine acetate → HCID 178458591, compound

HRID 450410Notes

Reaction equation

HRID 450410 reaction equation
F[C:2]1[CH:3]=[N:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:22]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[NH:20][N:19]=3)[C:14]([N+:27]([O-])=O)=[CH:13][CH:12]=2)[CH3:9])=[N:6][CH:7]=1.[C:30](O)(=O)C.C(N)=N>[Pd].C(O)C>[CH:24]([O:23][C:21]1[NH:20][N:19]=[C:18]([N:17]2[C:15]3=[N:16][C:11]([NH:10][C@H:8]([C:5]4[N:4]=[CH:3][CH:2]=[CH:7][N:6]=4)[CH3:9])=[CH:12][CH:13]=[C:14]3[N:27]=[CH:30]2)[CH:22]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 160693Formamidine acetateHCID 178458661HCID 178458661, compound2×

Product 1

HCID 178458591HCID 178458591, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The titled compound was prepared using a procedure similar to the one described for the synthesis of Example 6 using N6-[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]-N2-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridine-2,6-diamine (Intermediate 20) as the starting material. The starting material (1.7 g) was dissolved into ethanol (10 mL). To the solution was added Pd—C (0.3 g, 10%). A hydrogen inlet was introduced into the reaction flask. The resulting mixture was stirred for 5 hours. Formamidine acetate (2 g) was added to the resulting mixture. The mixture was stirred at 85° C. for 4 hours. The resulting mixture was filtered, and the filtrate was concentrated. The resulting residue was separated by Silica gel column. The title compound was obtained (0.14 g) as a by-product. LCMS: 365 [M+1]. 1H NMR (400 MHz, CD3OD) δ 8.60 (s, 2H), 8.20 (s, 1H), 7.60 (d, 1H), 7.20 (s, 2H), 6.50 (d, 1H), 6.10 (br, 1H), 5.10 (s, 1H), 4.70 (m, 1H), 1.40 (d, 3H), 1.30 (d, 6H).

Workup

  1. customThe titled compound was prepared
  2. additionA hydrogen inlet was introduced into the reaction flask
  3. stirringThe mixture was stirred at 85° C. for 4 hours
  4. filtrationThe resulting mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe resulting residue was separated by Silica gel column

Sources & evidence

ORD record
ord-04436907d76045c897b796b5655e1789
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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