Methanesulfonyl chloride → HCID 71230766, compound

HRID 589510Notes

Reaction equation

HRID 589510 reaction equation
[C:1]([C:5]1[CH:35]=[CH:34][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH:32]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH3:33])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:28][CH2:29][N:30]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:31][CH:32]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH3:33])=[O:10])=[CH:34][CH:35]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71231469HCID 71231469, compound

Product 1

HCID 71230766HCID 71230766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 39 (80 mg, 0.172 mmol) and TEA (0.048 ml, 0.344 mmol) in DCM was added methanesulfonyl chloride (0.021 ml, 0.258 mmol) dropwise. The resulting mixture was stirred at r.t. for 16 hrs, then quenched with water, and extracted with EtOAc. The organic layer was dried with Na2SO4 and filtered. The solvents were removed in vacuo, and the crude product was purified by flash chromatography (silica gel, EtOAc/MeOH/N H3 gradient) to yield Example 44.

Workup

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customThe solvents were removed in vacuo
  6. customthe crude product was purified by flash chromatography (silica gel, EtOAc/MeOH/N H3 gradient)
  7. customto yield Example 44

Sources & evidence

ORD record
ord-f52e420ba41f44c3be38ab585de36e87
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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