Diisopropylethylamine → HCID 71720822, compound

HRID 2205588Notes

Reaction equation

HRID 2205588 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.[O:34]=[C:35]1[NH:39][C:38]2[CH:40]=[CH:41][C:42]([S:44](Cl)(=[O:46])=[O:45])=[CH:43][C:37]=2[S:36]1>C(Cl)Cl>[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[N:18]([S:44]([C:42]3[CH:41]=[CH:40][C:38]4[NH:39][C:35](=[O:34])[S:36][C:37]=4[CH:43]=3)(=[O:46])=[O:45])[CH:11]([CH2:12][CH2:13][CH2:14]2)[C:10]1=[O:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 49127652-Oxo-2,3-dihydro-1,3-benzothiazole-6-sulfonyl chlorideHCID 78143630HCID 78143630, compound

Product 1

HCID 71720822HCID 71720822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-(3,4-Dimethoxyphenoxy)ethyl)-3,10-diazabicyclo[4.3.1]decan-2-one (15 mg, 0.05 mmol) in 3 ml DCM was treated with DIPEA (12 mg, 0.09 mmol) and stirred for 30 min at room temperature followed by addition of 2-oxo-2,3-dihydrobenzo[d]thiazole-6-sulfonyl chloride (22 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-HPLC in 55-65% buffer B in 16 mins.

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-HPLC in 55-65% buffer B in 16 mins

Sources & evidence

ORD record
ord-77390862c5894674affa820bea4ce26b
Source dataset
uspto-grants-2016_06
Patent number
US09371322B2

Reaction notes

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