Diisopropylethylamine → 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 2375808Notes

Reaction equation

HRID 2375808 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:8]([OH:10])=O)[NH:5][C:6]=1[CH3:7].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:45]([N:48]1[CH2:53][CH2:52][CH:51]([NH2:54])[CH2:50][CH2:49]1)([CH3:47])[CH3:46]>C(Cl)Cl>[CH:45]([N:48]1[CH2:53][CH2:52][CH:51]([NH:54][C:8]([C:4]2[NH:5][C:6]([CH3:7])=[C:2]([Br:1])[C:3]=2[CH3:11])=[O:10])[CH2:50][CH2:49]1)([CH3:47])[CH3:46]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 31633331-(Propan-2-yl)piperidin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 215256154-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid

Product 1

HCID 867607844-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amideYield 7.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid (570 mg) in DCM (15 mL) was added DIEA (2.11 g), HATU (994 mg) and 1-isopropyl-piperidin-4-ylamine (372 mg). The mixture was stirred for 16 h at RT after which it was concentrated. The residue was purified by preparative HPLC to give 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (65 mg) which was directly used in the next step.

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a0a2dbe64b7842418de750a4e4130c1a
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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