Water → HCID 23729497, compound

HRID 1911771Notes

Reaction equation

HRID 1911771 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:42][CH:43]2[CH2:45][CH2:44]2)[C:6]2[C:15]([CH2:16][N:17]([CH2:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=3)[C:18]3[N:19]=[N:20][N:21]([CH2:23][CH2:24][OH:25])[N:22]=3)=[CH:14][C:13]3[C:8](=[C:9]([CH3:41])[CH:10]=[CH:11][CH:12]=3)[N:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].O.[CH3:49]SC>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl>[F:36][C:33]([F:34])([F:35])[C:31]1[CH:32]=[C:27]([CH:28]=[C:29]([C:37]([F:39])([F:40])[F:38])[CH:30]=1)[CH2:26][N:17]([CH2:16][C:15]1[C:6]([N:5]([CH2:4][CH:1]2[CH2:2][CH2:3]2)[CH2:42][CH:43]2[CH2:45][CH2:44]2)=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:41])[C:18]1[N:19]=[N:20][N:21]([CH2:23][CH2:24][O:25][CH3:49])[N:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 23729469HCID 23729469, compound

Product 1

HCID 23729497HCID 23729497, compoundYield 367.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the 2-{5-[[2-(bis-cyclopropylmethyl-amino)-8-methyl-quinoline-3-ylmethyl]-(3,5-bistrifluoromethyl-benzyl)-amino]-tetrazol-2-yl}-ethanol (0.08 g, 0.126 mmol), (example 93), was added NaOH (0.010 g, 0.25 mmol) and water (1 mL). The reaction was stirred at room temperature for 15 min and then DCM (1 mL) was added followed by the addition of DMS (0.019 g, 0.15 mmol) and TBAB (0.002 g, 0.006 mmol). The reaction was continued for overnight. The solvent was evaporated and the aqueous layer was back extracted with DCM (2×10 mL). The combined organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated on rotavapor. The residue obtained was purified by preparative thin layer chromatography and eluted with 15% ethyl acetate and petroleum ether to get the desired product (0.30 g, 56%).

Workup

  1. waitThe reaction was continued for overnight
  2. customThe solvent was evaporated
  3. extractionthe aqueous layer was back extracted with DCM (2×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated on rotavapor
  7. customThe residue obtained
  8. customwas purified by preparative thin layer chromatography
  9. washeluted with 15% ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-60a59850d2c840b59a595657f8806107
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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