Water → HCID 71555922, compound

HRID 1497193Notes

Reaction equation

HRID 1497193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]([C:18]([NH:20][NH2:21])=[O:19])=[C:5]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:28](N1C=CN=C1)(N1C=CN=C1)=[S:29].C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]([C:18]1[O:19][C:28](=[S:29])[NH:21][N:20]=1)=[C:5]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 86683004HCID 86683004, compound

Product 1

HCID 71555922HCID 71555922, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

6-Chloro-4-phenyl-2-piperidin-1-yl-quinoline-3-carboxylic acid hydrazide (prepared as described in example 77 step E) (35 mg, 82.7 μmol, Eq: 1.00) and 1,1′-thiocarbonyldiimidazole (17.7 mg, 99.2 μmol, Eq: 1.2) were dissolved in THF (1.00 ml). Then triethylamine (11.7 mg, 16.1 μl, 116 μmol, Eq: 1.4) was added and the mixture was warmed to 50° C. for 72 h. Water was added and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 97:3) to afford the title compound as yellow solid (28 mg). MS (ESI): 423.1 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 97:3)

Sources & evidence

ORD record
ord-626829b93d2b440e95197d0269e1fd0c
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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