Hydrochloric Acid → HCID 11566789, compound

HRID 493429Notes

Reaction equation

HRID 493429 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[C:16]([C:21]([OH:23])=O)[CH:15]=[CH:14]3)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl.C(N1C=CN=C1)(N1C=CN=C1)=O.CO[CH:39]1[CH2:44][CH2:43][NH:42][CH2:41]C1>CN(C=O)C.CO>[N:42]1([C:21]([C:16]2[CH:15]=[CH:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([O:10][CH:7]4[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]4)[CH:12]=3)[N:17]=2)=[O:23])[CH2:41][CH:39]=[CH:44][CH2:43]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 682631,1'-CarbonyldiimidazoleHCID 776664-MethoxypiperidineHCID 57681576HCID 57681576, compound

Product 1

HCID 11566789HCID 11566789, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

6-(1-Isopropyl-piperidin-4-yloxy)-quinoline-2-carboxylic acid 1:1 hydrochloride (30 mg, 0.086 mmol, see intermediate 2) was dissolved in DMF (0.300 ml). 1,1′-Carbonyl-diimidazole (17 mg, 0.10 mmol) was added and the mixture was stirred for half an hour. 4-Methoxy-piperidine was added (6 mg, 0.014 mmol) and the mixture was stirred overnight. The mixture was diluted with 0.4 ml methanol and subjected to preparative HPLC purification on reversed phase material eluting with a gradient of acetonitrile/water/triethylamine. The product fractions were evaporated to dryness to yield 4.7 mg (14%) of the title compound as light brown solid. MS (m/e): 412.4 (MH+, 100%).

Workup

  1. stirringthe mixture was stirred overnight
  2. customsubjected to preparative HPLC purification on reversed phase material
  3. washeluting with a gradient of acetonitrile/water/triethylamine
  4. customThe product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-c95a1a87080849c58d344ad186c20c17
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

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