Sodium Methoxide → HCID 24751781, compound

HRID 1713115Notes

Reaction equation

HRID 1713115 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:25])[CH2:12][N:13]3[CH2:19][CH2:18][C:17]4[C:20](Cl)=[N:21][CH:22]=[N:23][C:16]=4[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH3:26][O-:27].[Na+]>CO>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:25])[CH2:12][N:13]3[CH2:19][CH2:18][C:17]4[C:20]([O:27][CH3:26])=[N:21][CH:22]=[N:23][C:16]=4[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59463660HCID 59463660, compound

Product 1

HCID 24751781HCID 24751781, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 7-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4-chloro-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine (52 mg, 0.14 mmol) in MeOH, a solution of NaOMe in MeOH (0.3 ml, 25% in MeOH) is added. The mixture is stirred at rt overnight. The solvent is removed and water is added to the residue. The mixture is extracted with DCM. The organic layer is washed with brine, dried and solvent evaporated to give the crude product, which is purified by PTLC (5% TEA in EtOAc) to afford the title compound. 1H NMR (CDCl3) δ 8.49 (s, 1H), 3.94 (s, 3H), 3.62 (m, 4H), 3.30 (s, 2H), 3.04 (m, 2H), 2.88 (m, 2H), 2.74-2.62 (m, 5H), 2.31 (m, 4H), 2.04 (m, 2H), 1.88 (m, 2H), 1.68 (m, 2H).

Workup

  1. customThe solvent is removed
  2. additionwater is added to the residue
  3. extractionThe mixture is extracted with DCM
  4. washThe organic layer is washed with brine
  5. customdried
  6. customsolvent evaporated
  7. customto give the crude product, which
  8. customis purified by PTLC (5% TEA in EtOAc)

Sources & evidence

ORD record
ord-7ab93f92862c43d9bc13b1455f5e6958
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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