Triethylamine → HCID 178438858, compound

HRID 1725186Notes

Reaction equation

HRID 1725186 reaction equation
[C:1]1([C:7]2[N:8]([CH2:21][C:22]([OH:24])=O)[C:9]([CH:12]3[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)(O)O.[NH2:41][C:42]([NH2:44])=[NH:43].C(N(CC)CC)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]1([C:7]2[N:8]([CH2:21][C:22]([NH:43][C:42]([NH2:44])=[NH:41])=[O:24])[C:9]([CH:12]3[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][CH3:20])[CH2:14][CH2:13]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 286947Carbonic acid-guanidine (1:1)HCID 57423722[2-Phenyl-5-(4-propyl-cyclohexyl)-pyrrol-1-yl]-acetic acid

Product 1

HCID 178438858HCID 178438858, compoundYield 145.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.91 g (2.8 mmol) [2-phenyl-5-(4-propyl-cyclohexyl)-pyrrol-1-yl]-acetic acid in 28 mL anhydrous DMF was added 2.27 g (14 mmol) carbonyldiimidazole. The reaction was stirred at room temperature for 50 min, upon which time was added 2.52 g (14 mmol) guanidine carbonate, 0.17 g (1.4 mmol) 4-dimethylaminopyridine, and 2.83 g (28 mmol) triethylamine. The reaction was stirred at room temperature over 16 hr. The solution was filtered to remove the precipitate that formed, was diluted with ethyl acetate, and was washed three times with brine. Drying over MgSO4 and concentration afforded 1.49 g of N-{2-[2-phenyl-5-(4-propyl-cyclohexyl)-pyrrol-1-yl]-acetyl}-guanidine as a yellow-brown oil. The product was observed to contain DMF by 1H NMR. However, it was used in the next step without further purification.

Workup

  1. stirringThe reaction was stirred at room temperature over 16 hr
  2. filtrationThe solution was filtered
  3. customto remove the precipitate
  4. customthat formed
  5. washwas washed three times with brine
  6. dry with materialDrying over MgSO4 and concentration

Sources & evidence

ORD record
ord-f50e165767a5413780ba2f1102572433
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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