Isopropylamine → N-isopropyl-1H-pyrrole-3-carboxamide

HRID 1435477Notes

Reaction equation

HRID 1435477 reaction equation
CC[N:3](C(C)C)[CH:4]([CH3:6])[CH3:5].[NH:10]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11]1.C(N)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH:4]([NH:3][C:15]([C:12]1[CH:13]=[CH:14][NH:10][CH:11]=1)=[O:17])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 101030Pyrrole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57937383N-isopropyl-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 isopropylamine (118 mg, 170 uL, 2.0 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: 80 mg (52%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.19 (d, J=6.64 Hz, 6 H), 3.95-4.31 (m, 1 H), 6.52 (dd, J=2.93, 1.56 Hz, 1 H), 6.70 (dd, J=2.93, 2.15 Hz, 1 H), 7.31 (t, J=1.76 Hz, 1 H), 7.58 (s, 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-3adcd8e89e8f4f43819d683bc86083f2
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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