Guanidine Hydrochloride → HCID 178513102, compound

HRID 1725172Notes

Reaction equation

HRID 1725172 reaction equation
[C:1]([C:9]1[N:10]([CH2:20][C:21]([OH:23])=O)[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:37][C:38]([NH2:40])=[NH:39].C(N(CC)CC)C>CN(C=O)C>[NH2:39][C:38](=[NH:37])[NH:40][C:21](=[O:23])[CH2:20][N:10]1[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH:13]=[C:9]1[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 57423708HCID 57423708, compound

Product 1

HCID 178513102HCID 178513102, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyl(2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetate (148 mg, 0.41 mmol) in trifluoroacetic acid was stirred for 2 h at room temperature. After removal of trifluoroacetic acid, the residue was treated with CH2Cl2 (10 ml), MeOH (1 ml) and H2O (10 ml). The two layers were separated and the aqueous was extracted with CH2Cl2 (3×10 ml). The combined organic extracts were washed with H2O (10 ml), brine (10 ml), dried (Na2SO4) filtered and concentrated. The crude material was purified by chromatography (silica gel, EtOAc/hexane/HCO2H: 10/40/0.1) to afford (2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetic acid (125 mg, 100%) as an oil. To a stirred solution of (2-benzoyl-5-phenyl-1H-pyrrol-1-yl)acetic acid (260 mg, 0.85 mmol) in DMF (2.0 ml) was added 1,1′-carbonyldiimidazole (166 mg, 1.02 mmol) at room temperature. After stirring for 1 h, the reaction mixture was treated with a solution of guanidine hydrochloride (244 mg, 2.55 mmol) in DMF (2.5 ml) and triethylamine (0.54 ml, 2.55 mmol). After stirring over night, the reaction mixture was quenched with H2O (30 ml). The aqueous was extracted with Et2O (3×30 ml), EtOAc (10 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The crude material was purified by chromatography (silica gel; EtOAc/hexane/2M NH3 in MeOH: 65/35/1) to give the titled compound (169 mg, 58%) as a white solid: mp 201-203° C.; MS (−) ES, 345 (M−H)−.

Workup

  1. stirringAfter stirring over night
  2. customthe reaction mixture was quenched with H2O (30 ml)
  3. extractionThe aqueous was extracted with Et2O (3×30 ml), EtOAc (10 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by chromatography (silica gel; EtOAc/hexane/2M NH3 in MeOH: 65/35/1)

Sources & evidence

ORD record
ord-5ce4103a9a4641f0afdac0f24b9a4c96
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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