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

HRID 1261731Notes

Reaction equation

HRID 1261731 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-253dc34c1fdd45658531482a15e4f0ad
Source dataset
uspto-grants-2013_06
Patent number
US08471026B2

Reaction notes

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