Ethanolamine → HCID 68488701, compound

HRID 1874996Notes

Reaction equation

HRID 1874996 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9]([C:11]([OH:13])=O)=[CH:8][C:7]=1[CH3:14])=[O:5])[CH3:2].CCN(C(C)C)C(C)C.[CH2:24]([CH2:26][NH2:27])[OH:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:25][CH2:24][CH2:26][NH:27][C:11]([C:9]1[NH:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:7]([CH3:14])[CH:8]=1)=[O:13]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68483604HCID 68483604, compound

Product 1

HCID 68488701HCID 68488701, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[(ethyloxy)carbonyl]-4-methyl-1H-pyrrole-2-carboxylic acid (0.160 g, 0.812 mmol) in DMF (4 ml) was added DIPEA (0.140 mL, 0.790 mmol). The reaction mixture was stirred and the solution was divided into four equal portions, one of which was added to a glass vial with a stir bar. To the vial was added ethanolamine (0.012 mL, 0.2 mmol) and HATU (0.075 g, 0.197 mmol) and the reaction mixture stirred overnight. Purification was accomplished by RPHPLC (water:acetonitrile with 0.1% TFA). The desired fractions were collected and lypholized to afford ethyl 5-{[(2-hydroxyethyl)amino]carbonyl}-3-methyl-1H-pyrrole-2-carboxylate (0.010 g, 48%) as an oil. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.63 (br. s., 1H) 8.25-8.42 (m, 1H) 6.61 (s, 1H) 4.25 (q, 2H) 3.48 (t, 2H) 3.28 (q, 2H) 2.25 (s, 3H) 1.30 (t, 3H). MS: m/z 241.4 (M+1).

Workup

  1. additionwas added to a glass vial with a stir bar
  2. stirringthe reaction mixture stirred overnight
  3. customPurification
  4. customThe desired fractions were collected

Sources & evidence

ORD record
ord-b245207796a346dbb0cdfabe136cc61e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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