Benzenesulfonyl chloride → HCID 50942945, compound

HRID 2045805Notes

Reaction equation

HRID 2045805 reaction equation
[CH3:1][C:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH2:5][CH2:6][N:7]1[C@H:12]2[CH2:13][CH2:14][C@@H:8]1[CH2:9][CH:10]([N:15]1[C:19]([CH:20]([CH3:22])[CH3:21])=[N:18][N:17]=[C:16]1[CH3:23])[CH2:11]2)[CH2:3][NH2:4].C(N(C(C)C)CC)(C)C.[C:39]1([S:45](Cl)(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[CH3:1][C:2]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH2:5][CH2:6][N:7]1[C@H:8]2[CH2:14][CH2:13][C@@H:12]1[CH2:11][CH:10]([N:15]1[C:19]([CH:20]([CH3:22])[CH3:21])=[N:18][N:17]=[C:16]1[CH3:23])[CH2:9]2)[CH2:3][NH:4][S:45]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 70805136HCID 70805136, compound

Product 1

HCID 50942945HCID 50942945, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of intermediate 24 (158 mg, 0.4 mmol) in CH2Cl2 (4 mL) was added diisopropylethylamine (0.175 mL, 1.0 mmol) followed by phenylsulfonyl chloride (0.065 mL, 0.5 mmol) and the solution stirred at room temperature under nitrogen atmosphere for 18 h. The reaction was concentrated in vacuo and purified by silica gel chromatography eluting with 0-5% methanol/CH2Cl2 to give the title compound (150 mg, 70%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by silica gel chromatography
  3. washeluting with 0-5% methanol/CH2Cl2

Sources & evidence

ORD record
ord-f42a629fb9854ff3bbf2b17991caf573
Source dataset
uspto-grants-2013_11
Patent number
US08592395B2

Reaction notes

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