Triethylamine → HCID 11591010, compound

HRID 1992405Notes

Reaction equation

HRID 1992405 reaction equation
Cl.Cl.Cl.[NH2:4][CH2:5][CH2:6][N:7]1[CH2:14][CH:13]2[O:15][CH:9]([CH2:10][N:11]([CH2:16][CH2:17][O:18][C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[CH2:12]2)[CH2:8]1.[CH3:27][C:28]1[C:32]([S:33](Cl)(=[O:35])=[O:34])=[C:31]([CH3:37])[O:30][N:29]=1.C(N(CC)CC)C>C(Cl)Cl>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][N:11]2[CH2:10][CH:9]3[O:15][CH:13]([CH2:14][N:7]([CH2:6][CH2:5][NH:4][S:33]([C:32]4[C:28]([CH3:27])=[N:29][O:30][C:31]=4[CH3:37])(=[O:35])=[O:34])[CH2:8]3)[CH2:12]2)=[CH:26][CH:25]=1)#[N:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 86625997HCID 86625997, compound

Product 1

HCID 11591010HCID 11591010, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{2-[7-(2-Amino-ethyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-ethoxy}benzonitrile tri hydrochloride salt (1 g, 2.35 mmol; Prep F) and 3,5-dimethylisoxazole-4-sulfonyl chloride (0.597 g, 3 mmol) were dissolved in DCM (25 mL). Triethylamine (1.95 mL, 3 mmol) was added and the reaction mixture was stirred at room temperature overnight under a nitrogen amosphere. The reaction mixture was concentrated and then redissolved in DCM (25 mL) and transferred to a phase separator. The DCM layer was washed with water (30 mL) and the layers were separated. The retained water was extracted with DCM (25 mL) and the layers were separated. The combined DCM fractions were concentrated under reduced pressure. Purification was performed by precipitation from a mixture of DCM, EtOAc and IPA to give a solid material (0.2 g, 17%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in DCM (25 mL)
  3. washThe DCM layer was washed with water (30 mL)
  4. customthe layers were separated
  5. extractionThe retained water was extracted with DCM (25 mL)
  6. customthe layers were separated
  7. concentrationThe combined DCM fractions were concentrated under reduced pressure
  8. customPurification
  9. customwas performed by precipitation from a mixture of DCM, EtOAc and IPA

Sources & evidence

ORD record
ord-c21f8b3fd6e14dc6ad4c77d1c8cd64a8
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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