Dimethylformamide → HCID 24883245, compound

HRID 2421071Notes

Reaction equation

HRID 2421071 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])([CH3:3])C.[CH:10]1([C:13]([OH:15])=O)[CH2:12][CH2:11]1.[CH3:16][N:17]([C:19]([O:23]N1N=NC2C=CC=NC1=2)=[N+:20]([CH3:22])[CH3:21])[CH3:18].F[P-](F)(F)(F)(F)F.[CH3:40][N:41]([CH:43]=O)C>>[CH:10]1([C:13]([N:41]2[CH2:43][CH2:8][CH:7]([N:4]3[CH2:1][CH2:3][CH:22]([N:20]4[C@H:21]5[CH2:13][CH2:10][CH2:11][CH2:12][C@@H:18]5[N:17]([CH3:16])[C:19]4=[O:23])[CH2:6][CH2:5]3)[CH2:9][CH2:40]2)=[O:15])[CH2:12][CH2:11]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 15655Cyclopropanecarboxylic 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 24883245HCID 24883245, compound

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 cyclopropanecarboxylic acid (32 μL, 0.4 mmol) at room temperature, the mixture was sonicated to dissolve the starting materials 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 residue was dissolved in dichloromethane (60 mL), the mixture was washed with 1N NaOH (5 mL) and brine (5 mL) and then concentrated in vacuo. The crude product was then purified by high pH prep-LCMS to provide the title compound as a white solid, which was converted to its HCl salt (60 mg, 78%). 1H NMR (400 MHz, METHANOL-D4) δ ppm 0.72-0.95 (m, 4H), 1.24-1.53 (m, 6H), 1.61 (d, J=12.50 Hz, 1H), 1.70 (d, J=14.06 Hz, 1H), 1.79-2.02 (m, 7H), 2.03-2.12 (m, 1H), 2.21-2.38 (m, 3H), 2.50-2.65 (m, 2H), 2.65 (s, 3H), 2.87-2.98 (m, 1H), 2.99-3.12 (m, 2H), 3.14 (d, J=13.28 Hz, 1H), 3.34 (s, 1H), 3.51-3.73 (m, 1H), 4.40 (d, J=13.28 Hz, 1H), 4.56 (d, J=12.89 Hz, 1H). MS (M+1): 389.2.

Workup

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

Sources & evidence

ORD record
ord-e2a5c83ee6ac4f2ab911b4adce1f7425
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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