Triethylamine → HCID 178513100, compound

HRID 1725175Notes

Reaction equation

HRID 1725175 reaction equation
[CH2:1]([C:8]1[N:9]([CH2:19][C:20]([OH:22])=O)[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)(O)O.[NH2:39][C:40]([NH2:42])=[NH:41].C(N(CC)CC)C>CN(C=O)C>[NH2:41][C:40](=[NH:39])[NH:42][C:20](=[O:22])[CH2:19][N:9]1[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=[C:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 286947Carbonic acid-guanidine (1:1)HCID 57423711HCID 57423711, compound

Product 1

HCID 178513100HCID 178513100, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of (2-benzyl-5-phenyl-1H-pyrrol-1-yl)acetic acid (155 mg, 0.53 mmol) in DMF (1.0 ml) was added 1,1′-carbonyldiimidazole (172 mg, 1.06 mmol) at room temperature. After 1 h stirring, the reaction mixture was treated with a solution of guanidine carbonate (286 mg, 1.59 mmol) in DMF (2.0 ml) and triethylamine (0.22 ml, 1.59 mmol). After stirring for 18 h, the reaction mixture was quenched with H2O (10 ml). The aqueous was extracted with EtOAc (3×30 ml). The combined organic extracts were washed with H2O (2×30 ml), brine (30 ml), dried (Na2SO4), filtered and concentrated. The crude material was purified by chromatography (silica gel; EtOAc/2M NH3 in MeOH: 97/3) to give the titled compound (130 mg, 74%) as a solid: mp 155-158° C.; MS (+) ES, 333 (M+H)+.

Workup

  1. stirringAfter stirring for 18 h
  2. customthe reaction mixture was quenched with H2O (10 ml)
  3. extractionThe aqueous was extracted with EtOAc (3×30 ml)
  4. washThe combined organic extracts were washed with H2O (2×30 ml), brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography (silica gel; EtOAc/2M NH3 in MeOH: 97/3)

Sources & evidence

ORD record
ord-8950bc9dbef44524af8d74b0a5891067
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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