Triethylamine → HCID 46203067, compound

HRID 1643484Notes

Reaction equation

HRID 1643484 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:17][CH2:16][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][CH2:8]2)[CH:2]=1.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[C:39]([CH3:41])[C:38]([S:42]([N:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH:46]2[CH2:51][CH2:52][CH2:53][S:54](Cl)(=[O:56])=[O:55])(=[O:44])=[O:43])=[C:37]([CH3:58])[CH:36]=1>C(Cl)Cl>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH3:58])[C:38]([S:42]([N:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH:46]2[CH2:51][CH2:52][CH2:53][S:54]([N:13]2[CH2:12][CH2:11][C:10]3([CH2:9][CH2:8][C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)([O:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)[CH2:15][CH2:14]2)(=[O:55])=[O:56])(=[O:44])=[O:43])=[C:39]([CH3:41])[CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59367776HCID 59367776, compoundHCID 59367806HCID 59367806, compound

Product 1

HCID 46203067HCID 46203067, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

9-(Pyridin-3-yl)-9-(2-(pyrrolidin-1-yl)ethoxy)-3-azaspiro[5.5]undecane (0.26 mmol, 1 eq) was dissolved in methylene chloride (3 ml) at 0° C., triethylamine (1.04 mmol, 4 eq) was added, and 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propane-1-sulfonyl chloride (0.26 mmol, 1 eq), dissolved in methylene chloride (2 ml) was added to the mixture. After 1 h at room temperature, the mixture was diluted with methylene chloride (20 ml). The organic phase was washed with water (10 ml) and saturated sodium chloride solution (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (1-5% methanol in methylene chloride). Yield: 47%. MS, Rt=3.6 min, m/z=731.5 [MH]+.

Workup

  1. additionwas added to the mixture
  2. washThe organic phase was washed with water (10 ml) and saturated sodium chloride solution (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (1-5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-7e9649ed972c4886a7c4302a4913e395
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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