Guanidine → HCID 178513099, compound

HRID 1725163Notes

Reaction equation

HRID 1725163 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[Na+].[Cl-].NC(N)=N.C[O:13][C:14](=O)[CH2:15][N:16]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[CH:19][CH:18]=[C:17]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C[O-].[Na+].CO.CS(C)=O>[C:33]1([C:17]2[N:16]([CH2:15][C:14]([NH:4][C:3]([NH2:5])=[NH:2])=[O:13])[C:20]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]4)=[CH:23][CH:22]=3)=[CH:19][CH:18]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 3520GuanidineHCID 5234Sodium ChlorideHCID 5742Guanidine HydrochlorideHCID 57423676HCID 57423676, compound

Product 1

HCID 178513099HCID 178513099, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 23694274Sodium methanolate methanolSolvent

Procedure

Guanidine HCl (700 mmol, 66.5 mg) is dissolved in 1 mL of 0.5M NaOMe/methanol solution and rotated to dryness. The residue is subsequently dissolved in 400 uL dry DMSO. A white NaCl precipitate remained and the supernatant (free guanidine base in solution) is added to a vial containing [2-phenyl-5-(4-piperidin-1-yl-phenyl)-pyrrol-1-yl]-acetic acid methyl ester (170 mmol, 64 mg). The solution is agitated in a shaker at room temperature. The reaction is quenched with excess AcOH (75 uL), concentrated in vacuo. The residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system.

Workup

  1. customThe reaction is quenched with excess AcOH (75 uL)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total)
  4. custompurified by Gilson preparative HPLC system

Sources & evidence

ORD record
ord-728f706d4e5b42c4a14667969f784f2a
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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