Triethylamine → HCID 178461877, compound

HRID 1820621Notes

Reaction equation

HRID 1820621 reaction equation
[N:1]1([C:10]([N:12]2C3C=CC=CC=3N=[N:13]2)=S)[C:5]2C=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C@@H:28]([NH2:30])[CH3:29])=[CH:24][CH:23]=1.NN1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](N)=O.[CH2:40]([N:42](CC)CC)C>C1COCC1>[CH:34]1([C:33]2[CH:37]=[C:10]([NH:1][C:5]3[C:4]4=[CH:9][CH:8]=[CH:7][N:3]4[N:2]=[C:40]([NH:30][C@H:28]([C:25]4[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=4)[CH3:29])[N:42]=3)[NH:12][N:13]=2)[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9128894314-19-6HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 178461877HCID 178461877, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of di(1H-benzo[d][1,2,3]triazol-1-yl)methanethione (3.0 g, 10.7 mmol) in THF (60 mL) was treated with (S)-1-(4-fluorophenyl)ethanamine (1.49 g, 10.7 mmol). The reaction was stirred at ambient temperature for 18 h and then 1-amino-1H-pyrrole-2-carboxamide (1.33 g, 10.7 mmol) was added, followed by triethylamine (2.9 mL, 10.7 mmol). The resulting mixture was warmed to 50° C. and stirred for 16 hours. The reaction mixture was concentrated, then diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (3×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2, 0% to 2% MeOH/CH2Cl2 gradient) to afford the desired compound as a solid (2.4 g, 73%). HPLC tR=2.636 min (Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4 4 min gradient, monitored at 220 nm). [M+H+]=307.33.

Workup

  1. temperatureThe resulting mixture was warmed to 50° C.
  2. stirringstirred for 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with EtOAc (50 mL)
  5. washwashed with saturated aqueous NaHCO3 (3×25 mL) and brine (25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (SiO2, 0% to 2% MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record
ord-c19ac465dc3c4370aa719cbdddbcc194
Source dataset
uspto-grants-2009_10
Patent number
US07605160B2

Reaction notes

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