Dimethylformamide → HCID 24883125, compound

HRID 2421073Notes

Reaction equation

HRID 2421073 reaction equation
[CH:1]([N:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH3:6])([CH3:3])C.[CH3:10][O:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]([OH:19])=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>>[CH3:10][O:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]([N:45]1[CH2:47][CH2:8][CH:7]([N:4]2[CH2:1][CH2:3][CH:26]([N:24]3[C@H:25]4[CH2:16][CH2:12][CH2:13][CH2:17][C@@H:22]4[N:21]([CH3:20])[C:23]3=[O:27])[CH2:6][CH2:5]2)[CH2:9][CH2:44]1)=[O:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 14834753-Methoxythiophene-2-carboxylic 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 24883125HCID 24883125, compoundYield 55%

Procedure

To a solution of (3aS,7aS)-1-(1,4′-bipiperidin-4-yl)octahydro-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-methoxythiophene-2-carboxylic acid (35 mg, 0.2 mmol) at room temperature, the mixture was then 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 (49 mg, 55%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.21-1.41 (m, 4H), 1.42-1.56 (m, 2H), 1.57-1.67 (m, 1H), 1.67-1.88 (m, 7H), 1.99 (d, J=8.98 Hz, 2H), 2.15-2.34 (m, 3H), 2.40-2.57 (m, 2H), 2.65 (s, 3H), 2.78-2.89 (m, 2H), 2.93 (t, J=9.96 Hz, 2H), 3.43 (s, 1H), 3.64-3.81 (m, 1H), 3.85 (s, 3H), 4.11-4.47 (m, 1H), 6.74 (d, J=5.47 Hz, 1H), 7.29 (d, J=5.47 Hz, 1H). MS (M+1): 461.2.

Workup

  1. customthe mixture was then 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 prep

Sources & evidence

ORD record
ord-488ba3a88ec847708ec4d67dc5357553
Source dataset
uspto-grants-2011_06
Patent number
US07956069B2

Reaction notes

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