Benzylamine → HCID 118046793, compound

HRID 596057Notes

Reaction equation

HRID 596057 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[C:15]([F:17])[C:11]([C:12](O)=[O:13])=[C:10]([C:18]#[N:19])[CH:9]=2)=[CH:6][C:5]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][N:3]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]2[CH:16]=[C:15]([F:17])[C:11]([C:12]([NH:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:13])=[C:10]([C:18]#[N:19])[CH:9]=2)=[CH:6][C:5]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 7504Benzylamine2×HCID 8471TriethylamineHCID 111923Propylphosphonic anhydride2×HCID 516892Sodium BicarbonateHCID 118046321HCID 118046321, compound

Product 1

HCID 118046793HCID 118046793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(2-amino-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)-2-cyano-6-fluorobenzoic acid were added DCM (1 mL), followed by benzylamine (0.017 mL, 0.153 mmol), triethylamine (0.053 mL, 0.383 mmol) and T3P (50% in EtOAc, 0.084 mL, 0.141 mmol). After 1 h more benzylamine (0.017 mL, 0.153 mmol) and T3P (50% in EtOAc, 0.084 mL, 0.141 mmol) were added and at 2 h the reaction was completed. Saturated NaHCO3 solution was added and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified on a silica gel column (heptane:EtOAc 1:0 to 0:1) to give the product as a colorless solid (17 mg). LCMS (m/z) 431.1 (MH+), 0.65 min. 1H NMR (400 MHz, CDCl3)) δ ppm 8.03 (s, 1H), 7.74 (s, 1H), 7.54 (d, 1H, J 12 Hz), 7.43-7.30 (m, 4H) 7.26 (s, 1H), 7.23 (s, 1H) 6.57 (br s, 1H), 4.74 (d, J 5.53 Hz, 2H), 4.10-4.06 (m, 2H), 3.55-3.46 (m, 2H), 2.77-2.67 (m, 1H), 1.80-1.70 (m, 4H).

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column (heptane:EtOAc 1:0 to 0:1)

Sources & evidence

ORD record
ord-c5dc572e10ec4bafa8f0a9edb0b4ef51
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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