Dimethylformamide → HCID 86605295, compound

HRID 490086Notes

Reaction equation

HRID 490086 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[CH:14][CH:15]=2)C=CC=CC=1.C1(OC(Cl)=O)C=CC=CC=1.[CH3:38][CH:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.CN(C=O)C>C(Cl)Cl>[CH:22]1([N:19]2[CH2:18][CH2:17][N:16]([C:13]3[N:12]=[CH:11][C:10]([NH:9][C:8]([N:42]4[CH2:43][CH2:44][CH:39]([CH3:38])[CH2:40][CH2:41]4)=[O:27])=[CH:15][CH:14]=3)[CH2:21][CH2:20]2)[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 15891Phenyl chloroformateHCID 693814-MethylpiperidineHCID 68405727HCID 68405727, compound

Product 1

HCID 86605295HCID 86605295, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 29 mg (0.08 mmol) [6-(4-cyclopentyl-piperazin-1-yl)-pyridin-3-yl]-carbamic acid phenyl ester (intermediately built from intermediate 6 and phenylchloroformate) and 12 mg (0.12 mmol) 4-methyl-piperidine (commercially available) in 1 ml DCM and 0.1 ml DMF was stirred at room temperature for 16 h. After evaporation the residue was taken up in methanol/DMF and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 13.6 mg (46%) of the title compound. (m/e): 372.3 (MH+; 100%).

Workup

  1. customAfter evaporation the residue
  2. customsubjected to preparative HPLC purification on reversed phase
  3. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  4. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-c8067015709f42ed87c2b5132d39e9e9
Source dataset
uspto-grants-2009_05
Patent number
US07528135B2

Reaction notes

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