Citric Acid → HCID 57572194, compound

HRID 602135Notes

Reaction equation

HRID 602135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10](NC)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26](O)=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O.O[N:34]1[C:38]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[C:16]([O:20][C:21]([N:23]1[CH2:31][CH2:30][CH2:29][CH:25]([C:26]([NH:34][CH2:38][C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH3:13])=[O:27])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

8

Reactant 6

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 672668402-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine

Product 1

HCID 57572194HCID 57572194, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Chlorophenyl)-4-methylthiazol-5-yl methylamine (477 mg, 2.00 mmol), 1-tert-butoxycarbonyl nipecotic acid (459 mg, 2.00 mmol) and 1-hydroxybenzotriazole monohydrate (368 mg, 2.40 mmol) were dissolved in N,N-dimethylformamide (10 mL). While this mixture was chilled in an ice bath, 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (460 mg, 2.40 mmol) and N-methylmorpholine (0.484 mL, 4.40 mmol) were added. The mixture was then stirred at room temperature for 6 hours. Subsequently, 5% aqueous citric acid was added and the mixture was extracted with ethyl acetate. The extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1) gave 916 mg (100%) of the desired compound as a colorless powder.

Workup

  1. temperatureWhile this mixture was chilled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed sequentially with a saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=5:1->1:1)

Sources & evidence

ORD record
ord-97e81394ce7748fda324e712d980606a
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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