Dimethylformamide → HCID 24883124, compound

HRID 2421072Notes

Reaction equation

HRID 2421072 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])([CH3:3])C.[CH3:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O.[CH3:20][N:21]([C:23]([O:27]N1N=NC2C=CC=NC1=2)=[N+:24]([CH3:26])[CH3:25])[CH3:22].F[P-](F)(F)(F)(F)F.[CH3:44][N:45]([CH:47]=O)C>>[CH3:26][N:24]1[C@H:25]2[CH2:10][CH2:11][CH2:12][CH2:13][C@@H:22]2[N:21]([CH:20]2[CH2:3][CH2:1][N:4]([CH:7]3[CH2:8][CH2:47][N:45]([C:13](=[O:15])[C:12]4[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=4[CH3:10])[CH2:44][CH2:9]3)[CH2:5][CH2:6]2)[C:23]1=[O:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 83732-Methylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 24883124HCID 24883124, compoundYield 51%

Procedure

To a solution of (3aS,7aS)-1-(1,4′-bipiperidin-4-yl)-3-methyloctahydro-2H-benzimidazol-2-one. 2HCl (71 mg, 0.18 mmol) in DMF (4 mL) was added diisopropylethylamine (0.1 mL, 0.57 mmol) and 2-methylbenzoic acid (30 mg, 0.2 mmol) at room temperature, the mixture was then sonicated to dissolve the starting material and HATU (75 mg, 0.2 mmol) was then added. The reaction mixture was stirred at room temperature and the solvent was removed under reduced pressure. The mixture was dissolved in dichloromethane (60 mL), washed with 1N NaOH (5 mL) and brine (5 mL) and then concentrated in vacuo. The residue was then purified by high pH prep. LCMS to provide the title compound as a white solid (44 mg, 51%). (HCl salt) 1H NMR (400 MHz, METHANOL-D4) δ ppm 1.23-1.56 (m, 5H), 1.60 (d, J=12.89 Hz, 1H), 1.69 (d, J=11.72 Hz, 1H), 1.74-1.96 (m, 6H), 1.97-2.11 (m, 2H), 2.23 (s, 3H), 2.15-2.38 (m, 3H), 2.51-2.62 (m, 2H), 2.64 (s, 3H), 2.83 (t, J=11.91 Hz, 1H), 2.94 (t, J=10.16 Hz, 1H), 3.04 (t, J=11.72 Hz, 3H), 3.39-3.54 (m, 1H), 3.57-3.71 (m, 1H), 4.74 (d, J=12.89 Hz, 1H), 7.03-7.42 (m, 4H). MS (M+1): 439.3.

Workup

  1. customthe mixture was then sonicated
  2. additionwas then added
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe mixture was dissolved in dichloromethane (60 mL)
  5. washwashed with 1N NaOH (5 mL) and brine (5 mL)
  6. concentrationconcentrated in vacuo
  7. customThe residue was then purified by high pH prep

Sources & evidence

ORD record
ord-fb45a2ea7d20486788e66933c6e823a1
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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