Guanidine Hydrochloride → HCID 178474435, compound

HRID 2117945Notes

Reaction equation

HRID 2117945 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].CO.C[O-].[Na+].[C:11]([NH:14][C:15]1[S:16][C:17]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[C:18]([CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26](OC)=[O:27])=[CH:24][CH:23]=2)[N:19]=1)(=[O:13])[CH3:12]>CN(C=O)C>[C:11]([NH:14][C:15]1[S:16][C:17]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([S:39]([CH3:42])(=[O:40])=[O:41])=[CH:37][CH:38]=2)=[C:18]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([NH:4][C:3]([NH2:5])=[NH:2])=[O:27])=[CH:30][CH:31]=2)[N:19]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 21914750HCID 21914750, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 178474435HCID 178474435, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Guanidine hydrochloride (152 mg) was dissolved in DMF (3 ml), and then 28% sodium methoxide methanol solution (0.3 ml) was added to the solution at r.t. The suspension was stirred at r.t. for 15 minutes, and methyl 4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)benzoate (150 mg) was added to the mixture at r.t. The reaction mixture was stirred at r.t. for 14 hours, and concentrated in vacuo. The residue was dissolved in water, and neutralized with 1N—HCl. The precipitate was collected through filtration, and purified by preparative silica gel chromatography with CHCl3/MeOH (10:1) as an eluent. The solid was washed with ethyl ether to give 4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)-N-[amino(imino)methyl]benzamide (36.6 mg) as an off-white solid.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 14 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. filtrationThe precipitate was collected through filtration
  5. custompurified by preparative silica gel chromatography with CHCl3/MeOH (10:1) as an eluent
  6. washThe solid was washed with ethyl ether

Sources & evidence

ORD record
ord-42cc1a8fa6444752a6705797cb2aa2a3
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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