Acetic Acid → HCID 178480814, compound

HRID 2377270Notes

Reaction equation

HRID 2377270 reaction equation
[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH:14]=O)[CH:11]=3)[C:4]=2[NH:5][N:6]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.CO>[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH2:14][N:20]4[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]4)[CH:11]=3)[C:4]=2[NH:5][N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 178519297HCID 178519297, compound

Product 1

HCID 178480814HCID 178480814, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 318 (980 mg, 3.16 mmol) in dichloromethane was added 1-methylpiperazine (0.83 mL, 7.5 mmol) and acetic acid (0.43 mL, 7.5 mmol) and the mixture was stirred at room temperature overnight. To this mixture was added sodium triacetoxyborohydride (1.0 g, 4.7 mmol) followed by methanol (5 mL) and stirring at room temperature was continued for about 2 days. The mixture was evaporated to dryness and the residue was purified by flash chromatography on silica gel using dichloromethane/methanol (9:1)+1% ammonium hydroxide as eluent to provide Example 607. MS (ESI): m/z 395 (M+H)+.

Workup

  1. stirringstirring at room temperature
  2. waitwas continued for about 2 days
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified by flash chromatography on silica gel
  5. customto provide Example 607

Sources & evidence

ORD record
ord-31b3a82c788347ebbd2f603f0328bddc
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…