Benzylamine → HCID 16223187, compound

HRID 1505637Notes

Reaction equation

HRID 1505637 reaction equation
Cl[C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:17])[N:3]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>CN1C(=O)CCC1>[CH2:18]([NH:25][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[CH:5]=[C:4]([CH3:17])[N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 86613559HCID 86613559, compound

Product 1

HCID 16223187HCID 16223187, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

A microwave reaction vessel was charged with 4-chloro-6-methyl-3-phenyl-thieno[3,2-c]pyridine (254 mg, 0.982 mmol), benzylamine (642 μl, 5.886 mmol), triethylamine (137 μl, 0.982), solvated in NMP (3 ml), and set to stir in a Biotage microwave reactor. The reaction was heated at 220° C. for 6 h. The crude reaction was next partitioned between ethyl acetate (25 ml) and distilled water (25 ml). The organic phase was dried (MgSO4) and the solvent removed in vacuo. Purification by flash column chromatography (petroleum spirit 40-60° C.:ethyl acetate, 5:1, Rf 0.5) afforded the title compound as a yellow solid (200.4 mg, 62%).

Workup

  1. customA microwave reaction vessel
  2. customThe crude reaction
  3. customwas next partitioned between ethyl acetate (25 ml)
  4. distillationdistilled water (25 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customPurification by flash column chromatography (petroleum spirit 40-60° C.:ethyl acetate, 5:1, Rf 0.5)

Sources & evidence

ORD record
ord-4819d53872e54cc3bd8c2a016b71e45c
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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