Ethylmorpholine → HCID 71239908, compound

HRID 705437Notes

Reaction equation

HRID 705437 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.C(N1CCOCC1)C.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH2:40][CH:41]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH3:53])[CH2:42][C:43]([O:45][CH3:46])=[O:44]>CN(C=O)C>[CH3:46][O:45][C:43](=[O:44])[CH2:42][CH:41]([NH:40][C:7]([C:5]1[N:6]=[C:2]([Br:1])[S:3][CH:4]=1)=[O:9])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[CH3:53]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 20696342HCID 20696342, compound

Product 1

HCID 71239908HCID 71239908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.48 mmol) of 2-bromo-1,3-thiazole-4-carboxylic acid are dissolved in 10 ml of DMF, N-ethylmorpholine (122 mg, 2.2 Eq) and TOTU (174 mg, 1.1 Eq) are added and the mixture is stirred at RT for 5 minutes. Then 93 mg (1 Eq) of methyl 3-amino-3-(2-methylphenyl)propanoate are added and the mixture is stirred overnight. The solvent is removed in vacuo and the residue subjected to preparative HPLC delivering 3-[(2-bromo-thiazole-4-carbonyl)-amino]-3-o-tolyl-propionic acid methyl ester yields in yields below 80%

Workup

  1. stirringthe mixture is stirred overnight
  2. customThe solvent is removed in vacuo
  3. customyields in yields below 80%

Sources & evidence

ORD record
ord-fa015e57d2e84221b99a31de27f0bf5f
Source dataset
uspto-grants-2015_11
Patent number
US09174952B2

Reaction notes

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