1-Methyl-2-pyrrolecarboxylic acid → HCID 58147289, compound

HRID 1847617Notes

Reaction equation

HRID 1847617 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.[CH3:10]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.N1[C:53]2[CH2:52][CH2:51][NH:50][CH2:49][C:48]=2[CH:47]=[CH:46][C:45]=1[C:54]([O:56][CH3:57])=[O:55]>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:50]1[CH2:51][CH2:52][C:53]2[C:48](=[CH:47][CH:46]=[C:45]([C:54]([O:56][CH3:57])=[O:55])[CH:10]=2)[CH2:49]1)=[O:9]

Participants

6

Reactant 4

HCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 56847101HCID 56847101, compound

Product 1

HCID 58147289HCID 58147289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a vial containing N-methylpyrrole-2-carboxylic acid (0.0206 g, 0.165 mmol) was added HATU (0.0627 g, 0.165 mmol) in DMF (1.00 mL) followed by DIPEA (0.157 mL, 0.9 mmol) in DMF (0.5 mL). The mixture was shaken at rt for 30 min before methyl 5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxylate hydrochloride (0.0343 g, 0.15 mmol) in DMF (1.00 mL) was added. The solution was then shaken at rt for 13 h. The solvent was evaporated and to the residue was added DCE (3 mL), water (1 mL), and a few drops of ammonia in MeOH (7 N). After being thoroughly mixed, the layers were separated and the aqueous layer was extracted with DCE (3 mL). The combined organic phases were then concentrated to give a solid residue.

Workup

  1. additionwas added
  2. customThe solvent was evaporated and to the residue
  3. additionwas added DCE (3 mL), water (1 mL), and a few drops of ammonia in MeOH (7 N)
  4. additionAfter being thoroughly mixed
  5. customthe layers were separated
  6. extractionthe aqueous layer was extracted with DCE (3 mL)
  7. concentrationThe combined organic phases were then concentrated
  8. customto give a solid residue

Sources & evidence

ORD record
ord-b7c2d5ed59d94cadbfe18fe71958de64
Source dataset
uspto-grants-2015_02
Patent number
US08952163B2

Reaction notes

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