Dimethylacetamide → HCID 46852596, compound

HRID 400526Notes

Reaction equation

HRID 400526 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:47]1[NH:52][CH2:51][CH2:50][N:49]2[CH2:53][CH2:54][CH2:55][C@H:48]12.CN(C)C(=O)C>CC1CCCO1>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]([C:4]([N:52]2[CH2:51][CH2:50][N:49]3[CH2:53][CH2:54][CH2:55][C@@H:48]3[CH2:47]2)=[O:6])=[CH:7][C:8]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 31374Dimethylacetamide2×HCID 23243772,4-Dichloro-5-[[(2-fluorophenyl)amino]sulfonyl]benzoic acidHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 46852596HCID 46852596, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Procedure

To 2,4-dichloro-5-{[(2-fluorophenyl)amino]sulfonyl}benzoic acid (800 mg, 2.197 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (919 mg, 2.416 mmol) in 2-methyltetrahydrofuran (15 mL) was added (R)-octahydropyrrolo[1,2-a]pyrazine (388 mg, 3.08 mmol). The reaction was stirred at room temperature for 45 minutes at which time N,N-dimethylacetamide (1 mL) was added. The reaction was stirred for an additional 45 minutes and N,N-dimethylacetamide (3 mL) was added. The reaction was stirred for an addition 2.5 hours, diluted with 2-methyltetrahydrofuran (15 mL), and washed with a solution of 6% sodium bicarbonate and 6% brine (2×15 mL). The aqueous layers were combined and re-extracted with 2-methyltetrahydrofuran (15 mL). The organic layer was washed with saturated brine (4×25 mL), dried over MgSO4, and concentrated. The residue was taken up in ethanol (20 mL) and reconcentrated to give the title compound.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for an addition 2.5 hours
  3. washwashed with a solution of 6% sodium bicarbonate and 6% brine (2×15 mL)
  4. extractionre-extracted with 2-methyltetrahydrofuran (15 mL)
  5. washThe organic layer was washed with saturated brine (4×25 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-584b65f02983455c883a0d3c51251253
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

Loading…