Formaldehyde → HCID 90412313, compound

HRID 1521966Notes

Reaction equation

HRID 1521966 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH2:12]3)=[CH:10][C:3]=12.FC(F)(F)C(O)=O.C=O.C([BH3-])#N.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:10][C:3]=12

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 90408209HCID 90408209, compound

Product 1

HCID 90412313HCID 90412313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 17E (200 mg, 0.6 mmol) in dichloromethane (10 mL) was added 0.5 mL trifluoroacetic acid and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated, dissolved in dichloromethane (20 mL), washed with sodium bicarbonate solution and concentrated. The residue was dissolved in methanol (2 mL) and treated with formaldehyde (120 mg, 37% in water) and sodium cyanoborohydride (57 mg, 0.9 mmol). The mixture was stirred at room temperature for 2 hours, diluted with dichloromethane and the organic phase was washed with water and concentrated to afford the title compound. LCMS: 250 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in dichloromethane (20 mL)
  3. washwashed with sodium bicarbonate solution
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methanol (2 mL)
  6. stirringThe mixture was stirred at room temperature for 2 hours
  7. washthe organic phase was washed with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dab29b31171e4b54b3ed31f2278c4a41
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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