Cyclopropylamine → N-cyclopropyl-1H-pyrrole-3-carboxamide

HRID 1435448Notes

Reaction equation

HRID 1435448 reaction equation
CC[N:3]([CH:7]([CH3:9])[CH3:8])C(C)C.[NH:10]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11]1.C1(N)CC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:7]1([NH:3][C:15]([C:12]2[CH:13]=[CH:14][NH:10][CH:11]=2)=[O:17])[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 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 57937310N-cyclopropyl-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the same procedure in Example 31, step B, using DIPEA (0.87 mL, 0.65 g, 5.0 mmol), 1H-pyrrole-3-carboxylic acid (0.25 g, 2.3 mmol), cyclopropylamine (0.14 g, 2.5 mmol) and HATU (1.0 g, 2.7 mmol) in DMF (10 mL). The crude product was purified by MPLC using EtOAc on silica gel to 52 mg (15%) of the title product. 1H NMR (400 MHz, METHANOL-D4) δ 0.42-0.63 (m, 2 H), 0.66-0.83 (m, 2 H), 2.60-2.80 (m, 1 H), 6.49 (dd, J=2.93, 1.56 Hz, 1 H), 6.69 (dd, J=2.73, 1.95 Hz, 1 H), 7.30 (t, J=1.76 Hz, 1 H).

Workup

  1. customThe crude product was purified by MPLC

Sources & evidence

ORD record
ord-8bdfc22779cb424fa063e5eb81281bad
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…