Methanol → HCID 22100287, compound

HRID 1457551Notes

Reaction equation

HRID 1457551 reaction equation
[CH2:1]([NH:8][C:9]([CH:11]1[N:16]([CH3:17])[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N:30]4[CH:34]=[N:33][N:32]=[CH:31]4)[CH:28]=3)[NH:23][CH:22]=2)[CH2:12]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.CO.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:1]([NH:8][CH2:9][CH:11]1[N:16]([CH3:17])[CH2:15][CH2:14][N:13]([CH2:18][CH2:19][CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N:30]4[CH:31]=[N:32][N:33]=[CH:34]4)[CH:28]=3)[NH:23][CH:22]=2)[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 22100283HCID 22100283, compound

Product 1

HCID 22100287HCID 22100287, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(N-benzylaminocarbonyl)-4-methyl-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperazine (29 mg, 0.06 mmol) in THF (5 mL) at room temperature, under nitrogen, was added borane-THF (1.0 mL of a 1.0M solution in THF, 1.0 mmol). The mixture was heated at reflux for 18 h, then cooled to room temperature. MeOH (2 mL) was added and the solvents evaporated. The residue was dissolved in EtOH (10 mL), and K2CO3 (17 mg, 0.13 mmol) was added. The mixture was heated at 75° C. for 20 h, before the solvent was evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 :MeOH:NH3 (95:5:1), to afford the amine (12 mg, 45%) as a gum. The title compound was characterised as its hydrogen oxalate salt. 1H nmr (360 MHz, d6 -DMSO) δ 1.80-1.96 (2H, m), 2.31 (3H, s), 2.37-2.62 (4H, m), 2.66-2.79 (3H, m), 2.80-3.06 (6H, m), 3.98 (1H, d, J=13.4 Hz), 4.03 (1H, d, J=13.4 Hz), 7.28-7.50 (8H, m), 7.78 (1H, s), 9.02 (2H, s), 11.12 (1H, br s). MS (ES+) 444 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. customthe solvents evaporated
  4. dissolutionThe residue was dissolved in EtOH (10 mL)
  5. temperatureThe mixture was heated at 75° C. for 20 h, before the solvent
  6. customwas evaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with CH2Cl2 :MeOH:NH3 (95:5:1)

Sources & evidence

ORD record
ord-63a9f051b06242ca90ca1d314d144c5e
Source dataset
uspto-grants-1998_12
Patent number
US05849746

Reaction notes

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