Diisopropylethylamine → HCID 71716538, compound

HRID 2205586Notes

Reaction equation

HRID 2205586 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[O:6][CH2:7][CH2:8][N:9]1[CH2:16][CH:15]2[NH:17][CH:11]([CH2:12][CH2:13][CH2:14]2)[C:10]1=[O:18].CCN(C(C)C)C(C)C.[S:33]1[C:37]2[CH:38]=[C:39]([S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:41][C:36]=2[N:35]=[CH:34]1>C(Cl)Cl>[S:33]1[C:37]2[CH:38]=[C:39]([S:42]([N:17]3[CH:15]4[CH2:14][CH2:13][CH2:12][CH:11]3[C:10](=[O:18])[N:9]([CH2:8][CH2:7][O:6][C:5]3[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:16]4)(=[O:43])=[O:44])[CH:40]=[CH:41][C:36]=2[N:35]=[CH:34]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27951701,3-Benzothiazole-6-sulfonyl chlorideHCID 78143559HCID 78143559, compound

Product 1

HCID 71716538HCID 71716538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-(3,4-Dimethoxyphenoxyl)ethyl)-3,9-diazabicyclo[3.3.1]nonan-2-one (32 mg, 0.1 mmol) in 3 ml DCM was treated with DIPEA (15 mg, 0.12 mmol) and stirring for 30 min at room temperature followed by addition of 1,3-benzothiazole-6-sulfonyl chloride (28 mg, 0.12 mmol). The reaction was stirred overnight at room temperature, the reaction was quenched with saturated NH4Cl solution (5 ml), extracted with DCM (4×10 ml). The organic layers were dried over MgSO4 and concentrated in vacuo. The mixture was purified with Preparative-TLC in 10% MeOH in CHCl3.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. customthe reaction was quenched with saturated NH4Cl solution (5 ml)
  3. extractionextracted with DCM (4×10 ml)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified with Preparative-TLC in 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-6265c47a52ab416cba9dfb29cb0adf74
Source dataset
uspto-grants-2016_06
Patent number
US09371322B2

Reaction notes

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