4-Toluenesulfonyl chloride → HCID 135977445, compound

HRID 1964611Notes

Reaction equation

HRID 1964611 reaction equation
[C:1]([NH:4][NH:5][C:6]([C:8]1[NH:9][C:10]([C:13]2[CH:18]=[C:17]([O:19][C@@H:20]([CH3:24])[CH2:21][O:22][CH3:23])[CH:16]=[C:15]([O:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([N:34]4[CH2:37][CH2:36][CH2:35]4)=[O:33])=[CH:28][C:27]=3[F:38])[CH:14]=2)=[CH:11][CH:12]=1)=O)(=[O:3])[CH3:2].C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[N:34]1([C:32]([C:29]2[CH:30]=[CH:31][C:26]([O:25][C:15]3[CH:14]=[C:13]([C:10]4[NH:9][C:8]([C:6]5[O:3][C:1]([CH3:2])=[N:4][N:5]=5)=[CH:12][CH:11]=4)[CH:18]=[C:17]([O:19][C@@H:20]([CH3:24])[CH2:21][O:22][CH3:23])[CH:16]=3)=[C:27]([F:38])[CH:28]=2)=[O:33])[CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 66683024HCID 66683024, compound

Product 1

HCID 135977445HCID 135977445, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N′-Acetyl-5-{3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrole-2-carbohydrazide (86 mg, 0.16 mmol) synthesized in Example (66h) was dissolved in dichloromethane (5 mL), and triethylamine (0.1 mL, 0.72 mmol) and p-toluenesulfonic acid chloride (69 mg, 0.36 mmol) were added, followed by stirring at room temperature overnight. The reaction solution was diluted with dichloromethane (60 mL), washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%) to afford the desired product (57 mg, yield 69%) as a white solid.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and subsequently dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%)

Sources & evidence

ORD record
ord-0609fa64e3144ca0a365e1abcabc59c5
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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