Methanesulfonyl chloride → HCID 9851485, compound

HRID 1637196Notes

Reaction equation

HRID 1637196 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[C:15]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:24][C:16]=2[S:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:1][S:2]([N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:14]1[C:15]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:24][C:16]=2[S:17][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 9845890HCID 9845890, compound2×

Product 1

HCID 9851485HCID 9851485, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.86 ml, 1.1 mmol) was added to a stirred solution of ethyl 3-[(2-aminophenyl)sulfanyl]-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 12 220 mg, 0.5 mmol) and N,N-diisopropylethylamine (0.2 ml, 1.1 mmol) in dichloromethane (3 ml). The mixture was left at ambient temperature for 20 hours and then diluted with dichloromethane and washed with water. The organics were dried (magnesium sulfate), and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using diethyl ether, and then ethyl acetate, as eluant. The title product was crystallised from diethyl ether to give a colourless solid (232 mg).

Workup

  1. washwashed with water
  2. dry with materialThe organics were dried (magnesium sulfate)
  3. customevaporated under reduced pressure
  4. customchromatographed on silica gel
  5. customThe title product was crystallised from diethyl ether

Sources & evidence

ORD record
ord-8e3fb9b97fbe4468ab067da4e88d18b3
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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