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

HRID 1771840Notes

Reaction equation

HRID 1771840 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 it 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-12966ffb5e3f41e2aa11741a65af40f5
Source dataset
uspto-grants-2016_02
Patent number
US09249142B2

Reaction notes

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