1-Methyl-2-pyrrolecarboxylic acid → HCID 67466941, compound

HRID 1619971Notes

Reaction equation

HRID 1619971 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]2[CH:51]([CH3:60])[CH:52]([CH2:57][CH2:58][CH3:59])[C:53](=[O:56])[NH:54][N:55]=2)=[CH:46][C:45]=1[OH:61]>C(Cl)Cl>[OH:61][C:45]1[CH:46]=[C:47]([C:50]2[CH:51]([CH3:60])[CH:52]([CH2:57][CH2:58][CH3:59])[C:53](=[O:56])[NH:54][N:55]=2)[CH:48]=[CH:49][C:44]=1[NH:43][C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=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 67466183HCID 67466183, compound

Product 1

HCID 67466941HCID 67466941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

240 mg (1.92 mmol) 1-methyl-1H-pyrrol-2-carboxylic acid is placed in 20 mL DCM. 760 mg (2.00 mmol) HATU, 1.50 mL (8.76 mmol) DIPEA and 600 mg (2.30 mmol) 6-(4-amino-3-hydroxy-phenyl)-5-methyl-4-propyl-4,5-dihydro-2H-pyridazin-3-one are added and the mixture is stirred for 3 h at RT. The reaction mixture is extracted successively with 0.5% acetic acid, 10% sodium carbonate solution and saline solution. Then the organic phase is dried and the solv. is eliminated i.V.

Workup

  1. extractionThe reaction mixture is extracted successively with 0.5% acetic acid, 10% sodium carbonate solution and saline solution
  2. customThen the organic phase is dried

Sources & evidence

ORD record
ord-d18e2d88031a4b4886977d95c9863671
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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