Dimethylformamide → HCID 24883123, compound

HRID 2421070Notes

Reaction equation

HRID 2421070 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])([CH3:3])C.[O:10]=[C:11]1[CH2:15][CH2:14][CH2:13][N:12]1[CH2:16][CH2:17][C:18]([OH:20])=O.[CH3:21][N:22]([C:24]([O:28]N1N=NC2C=CC=NC1=2)=[N+:25]([CH3:27])[CH3:26])[CH3:23].F[P-](F)(F)(F)(F)F.[CH3:45][N:46]([CH:48]=O)C>>[CH3:27][N:25]1[C@H:26]2[CH2:13][CH2:14][CH2:15][CH2:11][C@@H:23]2[N:22]([CH:21]2[CH2:3][CH2:1][N:4]([CH:7]3[CH2:8][CH2:48][N:46]([C:18](=[O:20])[CH2:17][CH2:16][N:12]4[CH2:13][CH2:14][CH2:15][C:11]4=[O:10])[CH2:45][CH2:9]3)[CH2:5][CH2:6]2)[C:24]1=[O:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 31466882-Oxo-1-pyrrolidinepropanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 24883123HCID 24883123, compoundYield 49%

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 3-(2-oxopyrrolidin-1-yl)propanoic acid (34 mg, 0.2 mmol) at room temperature, the mixture was sonicated to dissolve the starting materials and HATU (75 mg, 0.2 mmol) was then added. The solvent was removed under reduced pressure and the mixture was diluted in dichloromethane (60 mL). The mixture was washed with 1N NaOH (5 mL) and brine (5 mL) and concentrated in vacuo. The residue was then purified by high pH prep LCMS to provide the title compound as a white solid (44 mg, 49%). HCl salt-1H NMR (400 MHz, METHANOL-D4) δ ppm 1.24-1.53 (m, 4H), 1.53-1.71 (m, 1H), 1.76-2.11 (m, 7H), 2.10-2.37 (m, 4H), 2.41 (t, J=8.20 Hz, 3H), 2.55-2.81 (m, 4H), 2.66 (s, 3H), 2.87-3.01 (m, 1H), 3.05-3.22 (m, 3H), 3.39-3.67 (m, 8H), 3.74-3.89 (m, 1H), 4.14 (d, J=14.45 Hz, 1H), 4.67 (d, J=13.67 Hz, 1H). MS (M+1): 460.2

Workup

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

Sources & evidence

ORD record
ord-a4e7de5270704e4b88f011561db07bfd
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

Loading…