Triethylamine → HCID 58822100, compound

HRID 2104447Notes

Reaction equation

HRID 2104447 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[NH:21][C:22]([C:24]1[S:25][C:26]3[CH2:27][NH:28][CH2:29][CH2:30][C:31]=3[N:32]=1)=[O:23])=[O:13])=[CH:6]2.C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>N1C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[NH:21][C:22]([C:24]1[S:25][C:26]3[CH2:27][N:28]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:29][CH2:30][C:31]=3[N:32]=1)=[O:23])=[O:13])=[CH:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68451545HCID 68451545, compound

Product 1

HCID 58822100HCID 58822100, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (100 mg) obtained in Example 34 was dissolved in pyridine (3 mL), triethylamine (168 μl) and methanesulfonyl chloride (48 μl) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and methylene chloride and 1N hydrochloric acid were added to the residue to separate an organic layer. The resultant organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1) to give the title compound (79 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride and 1N hydrochloric acid
  2. additionwere added to the residue
  3. customto separate an organic layer
  4. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=100:1)

Sources & evidence

ORD record
ord-84b48762291e4a259cdec3dd81fe7735
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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