Pyridine → HCID 66893709, compound

HRID 1162066Notes

Reaction equation

HRID 1162066 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[C@H:17]([CH3:18])[CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:14]([CH3:26])[CH2:13]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1[S:36](Cl)(=[O:38])=[O:37].N1C=CC=CC=1>C(Cl)Cl>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][C:30]=1[S:36]([NH:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[C@H:17]([CH3:18])[CH2:16][N:15]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[C@@H:14]([CH3:26])[CH2:13]2)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1)(=[O:37])=[O:38]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 66892496tert-Butyl trans-4-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 66893709HCID 66893709, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl trans-4-[(5-amino-1-benzofuran-7-yl)methyl]-2,5-dimethylpiperazine-1-carboxylate (0.037 g, 0.1 mmol; obtained in Step 3) was dissolved in DCM and reacted with 2-methoxy-5-methylbenzenesulfonyl chloride (0.045 g, 0.2 mmol) and pyridine (0.024 g, 0.3 mmol) overnight. The mixture was washed with 1 M HCl and the organic layer was dried (MgSO4) and evaporated. The crude was purified using flashtube (10% MeOH in DCM) and afforded the title product (0.026 g, 48%). HPLC 93% RT=2.01 min (System A; 10-97% MeCN over 3 min), 93% RT=1.85 min (System B; 10-97% MeCN over 3 min). MS (ESI+) m/z 544.2 (M+H)+.

Workup

  1. washThe mixture was washed with 1 M HCl
  2. dry with materialthe organic layer was dried (MgSO4)
  3. customevaporated
  4. customThe crude was purified

Sources & evidence

ORD record
ord-b27806ac0d664bcd8203dad94aa3420a
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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