Triethylamine → HCID 18172419, compound

HRID 397056Notes

Reaction equation

HRID 397056 reaction equation
[CH3:1][C:2]1[C:6]([S:7](Cl)(=[O:9])=[O:8])=[C:5]([CH3:11])[O:4][N:3]=1.[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[CH:32][CH:31]=1)[NH:25][CH2:24][CH2:23]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(CC)CC>C1COCC1>[CH2:12]([O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[CH:32][CH:31]=1)[N:25]([S:7]([C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH3:11])(=[O:9])=[O:8])[CH2:24][CH2:23]2)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 181724176-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 18172419HCID 18172419, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethylisoxazole-4-sulfonyl chloride (0.034 g, 0.18 mmol) was added to a solution of 6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.075 g, 0.18 mmol) and Et3N (0.037 ml, 0.26 mmol) in anhydrous THF (10 ml) at rt under N2. The resulting suspension was stirred at rt for 21 hr, then evaporated in vacuo to a residue that was suspended in a mixture of saturated NaHCO3 solution (4 ml) and H2O (4 ml). This was extracted with CHCl3 (4×5 ml) and the combined extracts were dried over MgSO4, then concentrated in vacuo to give 0.110 g of yellow oil. Purification by flash chromatography, eluting with EtOAc:MeOH (1:1) gave 0.078 g (76% yield) of white solid.

Workup

  1. customevaporated in vacuo to a residue that
  2. additionwas suspended in a mixture of saturated NaHCO3 solution (4 ml) and H2O (4 ml)
  3. extractionThis was extracted with CHCl3 (4×5 ml)
  4. dry with materialthe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08a9d0d589564b77b253e3b5d765f5ef
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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