Oxalyl chloride → HCID 58488524, compound

HRID 451368Notes

Reaction equation

HRID 451368 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([OH:16])=O)[C:10]=1[CH3:17].C(Cl)(=O)C(Cl)=O.Cl.[CH3:25][S:26]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27].CCN(C(C)C)C(C)C>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:13][CH:12]=[C:11]([C:14]([NH:33][C:32]2[CH:31]=[CH:30][C:29]([S:26]([CH3:25])(=[O:28])=[O:27])=[CH:35][CH:34]=2)=[O:16])[C:10]=1[CH3:17]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27351804-(Methylsulfonyl)aniline hydrochlorideHCID 58488523HCID 58488523, compound

Product 1

HCID 58488524HCID 58488524, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-(2-chloro-4-fluorophenyl)-4-methyl-1H-pyrrole-3-carboxylic acid (0.61 g, 2.4 mmol) in dichloromethane (30 ml) was added oxalyl chloride (0.41 ml, 4.8 mmol). The mixture was stirred at room temperature for 2.0 h, after which time the solvent was removed on a rotary evaporator. To this brown residue was added THF (40 ml), 4-(methanesulfonyl)aniline hydrochloride (495 mg, 2.38 mmol), and DIEA (1.6 ml, 9.5 mmol). The solution was stirred at room temperature for 20 h. The reaction mixture was concentrated on a rotary evaporator and 2N HCl (30 ml) was added to the residue. The solid was filtered and washed with 2N HCl, water and IPE to give the title compound (812 mg, 84%) as a brown solid.

Workup

  1. customafter which time the solvent was removed on a rotary evaporator
  2. stirringThe solution was stirred at room temperature for 20 h
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator and 2N HCl (30 ml)
  4. additionwas added to the residue
  5. filtrationThe solid was filtered
  6. washwashed with 2N HCl, water and IPE

Sources & evidence

ORD record
ord-d75ee2fec5bc4710bc546c922848871f
Source dataset
uspto-grants-2013_07
Patent number
US08487117B2

Reaction notes

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