Methanesulfonyl chloride → HCID 20801141, compound

HRID 1071677Notes

Reaction equation

HRID 1071677 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[N:11]([CH2:19][C:20]3[CH:24]=[C:23]([C:25]4[S:26][C:27]([Cl:30])=[CH:28][CH:29]=4)[O:22][N:21]=3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:3][CH2:2]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl.CCN(CC)CC>[CH3:31][S:32]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[N:11]([CH2:19][C:20]3[CH:24]=[C:23]([C:25]4[S:26][C:27]([Cl:30])=[CH:28][CH:29]=4)[O:22][N:21]=3)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:3][CH2:2]1)(=[O:34])=[O:33]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20801153HCID 20801153, compound

Product 1

HCID 20801141HCID 20801141, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 50 mg 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid piperidin-4-ylamide in 2 ml DCM, 0.3 ml NEt3 and 20 mg Methanesulfonyl chloride were added at RT and stirred for 16 h. After removal of the solvent under reduced pressure the residue was directly purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). After lyophilization the product was obtained as a white solid.

Workup

  1. customAfter removal of the solvent under reduced pressure the residue
  2. customwas directly purified by preparative RP-HPLC
  3. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)
  4. customAfter lyophilization the product was obtained as a white solid

Sources & evidence

ORD record
ord-e5af98d47b3f4888b9400268940706a2
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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