Triethylamine → HCID 59513689, compound

HRID 1159942Notes

Reaction equation

HRID 1159942 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].[CH3:10][N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](Cl)=[O:17].C(N(CC)CC)C>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:16]([C:12]2[N:11]([CH3:10])[CH:15]=[CH:14][CH:13]=2)=[O:17])[CH:7]=[CH:8][CH:9]=1)#[CH:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chloride

Product 1

HCID 59513689HCID 59513689, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-ethynylaniline (10.35 g, 0.088 mol) in anhydrous THF (700 mL) under N2 was added dropwise 1-methylpyrrole-2-carboyl chloride (12.69 g, 0.088 mol). Triethylamine (15.0 mL, 0.108 mol) was added and the mixture was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4, filtered and concentrated to give a brownish solid that was triturated with diethyl ether to give 13.4 g (68%) of product. LCMS (AP)+ 225.2.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a brownish solid
  6. customthat was triturated with diethyl ether

Sources & evidence

ORD record
ord-1c2405ee70b249dea9027fb1b45452ec
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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