Diisopropylethylamine → N-methyl-1H-pyrrole-3-carboxamide

HRID 1435473Notes

Reaction equation

HRID 1435473 reaction equation
CC[N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.N1C=CC(C(O)=O)=C1.Cl.CN.[CH3:21][N:22]([C:24]([O:28]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:21][NH:22][C:24]([C:9]1[CH:6]=[CH:4][NH:3][CH:7]=1)=[O:28]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 101030Pyrrole-3-carboxylic acidHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 55284998N-methyl-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DIPEA (284 mg, 381 uL, 2.2 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid (111 g, 1.0 mmol) and methylamine hydrochloride (222 mg, 3.3 mmol) in DMF (10 mL) at 0° C. Stirring for 20 min, HATU (570 g, 1.5 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature, diluted with EtOAc (100 mL), washed with H2O (3×10 mL) and dried over Na2SO4. The crude product was purified by MPLC using EtOAc on silica gel. Yield: 57 mg (46%). 1H NMR (400 MHz, CHLOROFORM-D) δ 2.89 (s, 3 H), 5.89 (s, 1 H), 6.36-6.44 (m, 1 H), 6.75-6.79 (m, 1 H), 7.34-7.40 (m, 1 H).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. washwashed with H2O (3×10 mL)
  3. dry with materialdried over Na2SO4
  4. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-b34a7433d76148d0a083dd01a9db4165
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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