1,1,3,3-Tetramethylguanidine → HCID 178483393, compound

HRID 1370688Notes

Reaction equation

HRID 1370688 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N+:6]([CH3:38])([CH3:37])[CH2:7][CH:8]=[CH:9][C:10]1[CH2:17][S:16][CH:15]2[N:12]([C:13](=[O:33])[CH:14]2[NH:18][C:19](=[O:32])[CH2:20][S:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[C:11]=1[C:34]([Cl:36])=[O:35].Cl.[N:40]1(C(=N)N)[CH:44]=[N:43]C=N1.CN(C)C(=N)N(C)C>CS(C)=O>[ClH:36].[NH:2]([CH2:3][CH2:4][CH2:5][N+:6]([CH3:38])([CH3:37])[CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH2:17][S:16][C@H:15]2[N:12]([C:13](=[O:33])[C@H:14]2[NH:18][C:19](=[O:32])[CH2:20][S:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[C:11]=1[C:34]([Cl:36])=[O:35])[C:44]([NH2:43])=[NH:40]

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 162185151H-1,2,4-Triazole-1-carboximidamide--hydrogen chloride (1/1)HCID 131723931HCID 131723931, compound

Product 1

HCID 178483393HCID 178483393, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred suspension of 122 mg of (E)-(6R,7R)-3-[3-[(3-amino-propyl)-dimethyl-ammonio]-propenyl-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid chloride monohydrochloride in 2 ml of dimethylsulfoxide was added 60 mg of 1H-1,2,4-triazole-1-carboximidamide monohydrochloride followed by 0.05 ml of tetramethylguanidine. The mixture was stirred for 2 h at 20° and then subjected to chromatographic purification on MCI gel CHP20P using a gradient of 0-30% aqueous acetonitrile for elution. The product-containing fractions were concentrated in vacuo and freeze-dried, and the remaining amorphous material was triturated with 10 ml of a 0.4 N solution of hydrochloric acid in diethyl ether. The white solid was isolated by filtration, washed with 20 ml of diethyl ether and dried to give 48 mg of (E)-(6R,7R)-3-[3-[(3-guanidino-propyl)-dimethyl-ammonio]-propenyl]-7-[2-(naphthalen-2-ylsulfanyl)-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid chloride monohydrochloride as a white solid.

Workup

  1. customsubjected to chromatographic purification on MCI gel CHP20P
  2. washfor elution
  3. concentrationThe product-containing fractions were concentrated in vacuo
  4. customfreeze-dried
  5. customthe remaining amorphous material was triturated with 10 ml of a 0.4 N solution of hydrochloric acid in diethyl ether
  6. customThe white solid was isolated by filtration
  7. washwashed with 20 ml of diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-622bc91baa0e46e69ec472f13b5f5da7
Source dataset
uspto-grants-2003_06
Patent number
US06583133B1

Reaction notes

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