Dimethylformamide → HCID 178451357, compound

HRID 378988Notes

Reaction equation

HRID 378988 reaction equation
[NH:1]([C:5]1[S:6][C:7]([C:11]([OH:13])=O)=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3].CN(C=O)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:44][CH2:45][CH2:46][CH2:47][O:48][CH2:49][C:50]([O:52][CH2:53][CH2:54][CH2:55][CH3:56])=[O:51]>C(OCC)(=O)C>[NH:1]([C:5]1[S:6][C:7]([C:11]([NH:44][CH2:45][CH2:46][CH2:47][O:48][CH2:49][C:50]([O:52][CH2:53][CH2:54][CH2:55][CH3:56])=[O:51])=[O:13])=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86757461HCID 86757461, compoundHCID 178433209HCID 178433209, compound

Product 1

HCID 178451357HCID 178451357, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

175 mg of 2-guanidino-4-methyl-thiazole-5-carboxylic acid, 2.6 ml of DMF, 0.29 ml of N-MM and 332 mg of HBTU are stirred at room temperature (RT) for one hour, treated with 197 mg of butyl (3-amino-propoxy)-acetate hydrochloride and stirred at RT for a further 18 hrs. For the working up, the mixture is diluted with ethyl acetate, washed with dilute sodium carbonate solution, dilute sodium chloride solution and saturated sodium chloride solution, dried and evaporated in a vacuum. Chromatography on silica gel with methylene chloride-alcohol gives 162 mg of butyl {3-[(2-guanidino-4-methyl-thiazole-5-carbonyl)-amino]-propoxy}-acetate, mass spectroscopy (MS): 372 (M+H)+.

Workup

  1. washwashed with dilute sodium carbonate solution, dilute sodium chloride solution and saturated sodium chloride solution
  2. customdried
  3. customevaporated in a vacuum

Sources & evidence

ORD record
ord-687b268787bd424297635cf23ba3c159
Source dataset
uspto-grants-2001_10
Patent number
US06297266B1

Reaction notes

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