Triethylamine → HCID 136054480, compound

HRID 606514Notes

Reaction equation

HRID 606514 reaction equation
O[CH:2]([CH:34]([CH3:36])[CH3:35])[CH2:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH:20][C:21]([C:23]3[NH:32][C:31](=[O:33])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[O:22])[CH:14]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].C(N(CC)CC)C.CS(Cl)(=O)=O>C1COCC1.C(OCC)(=O)C>[CH3:35][CH:34]([CH3:36])/[CH:2]=[CH:3]/[S:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][NH:20][C:21]([C:23]3[NH:32][C:31](=[O:33])[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)=[O:22])[CH:14]=2)=[CH:11][CH:12]=1)(=[O:5])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 136054518HCID 136054518, compound

Product 1

HCID 136054480HCID 136054480, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-([4′-[(2-hydroxy-3-methylbutyl)sulfonyl]biphenyl-3-yl]methyl)-4-oxo-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 105 (0.300 g, 0.593 mmol) and triethylamine (0.579 mL, 4.15 mmol) in THF (6 mL) was added dropwise methanesulfonyl chloride (0.083 mL, 1.07 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate, washed with 0.1N hydrochloric acid and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was crystallized from ethyl acetate-diethyl ether to give the title compound as a pale-yellow powder (0.220 g, 76%).

Workup

  1. washwashed with 0.1N hydrochloric acid and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-7957a395caa04452a694464e08e837cb
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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