1,2-Dichloroethane → HCID 11754542, compound

HRID 225773Notes

Reaction equation

HRID 225773 reaction equation
C(Cl)CCl.C(N(C(C)C)CC)(C)C.C(N)C1C=CC=CC=1.[CH3:22][C:23]1[CH:39]=[CH:38][C:26]([C:27]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]2[C:35](O)=O)=[O:28])=[CH:25][CH:24]=1.[CH2:40]([NH:47][C:48]([C:50]1[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][C:51]=1[NH-:57])=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>>[CH2:40]([N:47]1[C:48](=[O:49])[C:50]2[C:51](=[CH:52][C:53]([Cl:56])=[CH:54][CH:55]=2)[N:57]=[C:35]1[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][N:29]1[C:27](=[O:28])[C:26]1[CH:38]=[CH:39][C:23]([CH3:22])=[CH:24][CH:25]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 167698421-(4-Methylbenzoyl)piperidine-2-carboxylic acidHCID 178514215HCID 178514215, compound

Product 1

HCID 11754542HCID 11754542, compoundYield 47%

Procedure

Formula 205 where T is a covalent bond; W, X, Y and Z are —C═; U—V is —N(R6)—CReRf—CRgRh—; R1, R2, R4 and Ra to Rh are H; Rand R6 is p-methyl-benzoyl: A mixture of the compound of Formula 203 (2.66 g, 6.7 mmol), 1M NaOH (27 mL), methanol (54 mL), and dioxane (36 mL) was stirred at room temperature for 7 hours. The solvents were evaporated and the residue portioned between dichloromethane (75 mL), saturated NaCl (50 mL), and concentrated HCl (3 mL). The layers were separated and the organic layer dried over MgSO4 and concentrated under vacuum to give the corresponding compound of Formula 204, 4-chloro-2-[1-(4-methyl-benzoyl)-piperidine-2-carbonyl]amino}-benzoic acid, which was carried forward without further purification. This crude product was redissolved in dichloromethane and treated with EDC (3.84 g, 20 mmol), and diisopropylethylamine (3.50 mL, 20 mmol). After stirring 20 minutes, benzylamine (2.20 mL, 20 mmol) was added and the mixture stirred overnight at room temperature. The mixture was washed with water (2×50 mL) and 1M HCl, dried over MgSO4, filtered and concentrated under vacuum to give 1.5 g (47% yield) of the desired product of Formula 205, 1-(4-methyl-benzoyl)-piperidine-2-carboxylic acid (2-benzylcarbamoyl-5-chloro-phenyl-amide, a crude product that was found to be 80% pure by reverse phase HPLC. The product was taken on without further purification. LRMS (MH+) m/z 491.

Workup

  1. customwas carried forward without further purification
  2. dissolutionThis crude product was redissolved in dichloromethane
  3. stirringthe mixture stirred overnight at room temperature
  4. washThe mixture was washed with water (2×50 mL) and 1M HCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-879cb533180c4014998c1edc2da0fde4
Source dataset
uspto-grants-2009_07
Patent number
US07557115B2

Reaction notes

Loading…