Ammonia → N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide

HRID 1964842Notes

Reaction equation

HRID 1964842 reaction equation
[C:1]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH2:14][CH2:13][S:12][CH:11]2[C:15]([NH:17][CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](O)=[O:20])=[O:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH3:34].O1CCOCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:34][C:19](=[O:20])[CH:18]([NH:17][C:15]([CH:11]1[N:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:6][CH:5]=2)(=[O:9])=[O:8])[CH2:14][CH2:13][S:12]1)=[O:16])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10128046({[3-(Biphenyl-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)(phenyl)acetic acid

Product 1

HCID 10288863N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamideYield 80%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound Ia, e.g., ({[3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)-(phenyl)acetic acid (500 mg, 1.04 mmol) was dissolved in THF (10 mL). Ammonia in dioxane (0.5N, 3.11 mL, 1.55 mmol) was added followed by HOBt (210 mg, 1.55 mmol) and DMAP (6 mg, 0.05 mmol). EDC.HCl (298 mg, 1.55 mmol) was finally added. The mixture was stirred for 5 hours at RT. As the reaction was complete, it was diluted with EtOAc, washed with 5% citric acid, NH4Cl sat, NaHCO3 sat, brine and dried over MgSO4. After filtration and evaporation of the solvents, the resulting crude product was purified by flash chromatography (Cyclohexane/EtOAc, gradient from 1:1 to 0:1). Compound Ib, e.g. N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide, was isolated in 90% purity by HPLC (349 mg, 80% yield).

Workup

  1. washwashed with 5% citric acid, NH4Cl
  2. dry with materialbrine and dried over MgSO4
  3. filtrationAfter filtration and evaporation of the solvents
  4. customthe resulting crude product was purified by flash chromatography (Cyclohexane/EtOAc, gradient from 1:1 to 0:1)

Sources & evidence

ORD record
ord-d2948a529924486ca6d60a648d3e4907
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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