Diisopropylethylamine → HCID 71718374, compound

HRID 2205587Notes

Reaction equation

HRID 2205587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[O:6][CH2:7][CH2:8][N:9]1[CH2:17][CH2:16][CH:15]2[NH:18][CH:11]([CH2:12][CH2:13][CH2:14]2)[C:10]1=[O:19].CCN(C(C)C)C(C)C.[S:34]1[C:38]2[CH:39]=[C:40]([S:43](Cl)(=[O:45])=[O:44])[CH:41]=[CH:42][C:37]=2[N:36]=[CH:35]1>C(Cl)Cl>[S:34]1[C:38]2[CH:39]=[C:40]([S:43]([N:18]3[CH:15]4[CH2:14][CH2:13][CH2:12][CH:11]3[C:10](=[O:19])[N:9]([CH2:8][CH2:7][O:6][C:5]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:17][CH2:16]4)(=[O:44])=[O:45])[CH:41]=[CH:42][C:37]=2[N:36]=[CH:35]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27951701,3-Benzothiazole-6-sulfonyl chlorideHCID 78143630HCID 78143630, compound

Product 1

HCID 71718374HCID 71718374, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-(3,4-Dimethoxyphenoxy)ethyl)-3,10-diazabicyclo[4.3.1]decan-2-one (24 mg, 0.07 mmol) in 3 ml DCM was treated with DIPEA (11 mg, 0.09 mmol) and stirred for 30 min at room temperature followed by addition of 1,3-benzothiazole-6-sulfonyl chloride (20 mg, 0.09 mmol). After stirring 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. stirringAfter stirring 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-cad190b7850346e7bc9a38180c44c131
Source dataset
uspto-grants-2016_06
Patent number
US09371322B2

Reaction notes

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