Water → HCID 69063894, compound

HRID 1725156Notes

Reaction equation

HRID 1725156 reaction equation
[C:1]1([C:7]2N(CC(O)=O)[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3]C=1.C1N=C[N:24]([C:27]([N:29]2[CH:33]=[N:32][CH:31]=[CH:30]2)=O)C=1.Cl.[NH2:35]C(N)=N.C(N(CC)CC)C.[OH2:46]>CN(C=O)C>[NH2:35][C:27]([NH2:24])=[N:29][C:30](=[O:46])[CH2:31][N:32]1[CH:33]=[C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[C:11]1[C:7]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:1]=1

Participants

7

Reactant 5

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 16090340HCID 16090340, compound

Product 1

HCID 69063894HCID 69063894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2,5-diphenyl-pyrrol-1-yl)-acetic acid (1 eq.) in DMF is added CDI (1.2 eq.) and the mixture stirred at RT for 1 hour. Then add a solution of guanidine HCl (3 eq.) and triethylamine (3 eq.) in DMF is added. The reaction is stirred for 5 hours, then water is added and the mixture extracted with EtOAc, dried over MgSO4 and concentrated. The residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system. See Gilson Preparative HPLC conditions: Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 μM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.

Workup

  1. additionis added
  2. stirringThe reaction is stirred for 5 hours
  3. extractionthe mixture extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. dissolutionThe residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total)
  7. custompurified by Gilson preparative HPLC system
  8. custom2 min
  9. custom14 min
  10. custom10% A, 15 min
  11. custom10% A, 16 min

Sources & evidence

ORD record
ord-4b30e4bcc2a2471f90cd4a9ea4ba6176
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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