Triethylamine → HCID 68522068, compound

HRID 1992407Notes

Reaction equation

HRID 1992407 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[CH2:12][CH:11]2[O:13][CH:7]([CH2:8][N:9]([CH2:14][CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=3[F:25])[CH2:10]2)[CH2:6]1.[F:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>C(Cl)Cl>[C:21]([C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:15][CH2:14][N:9]2[CH2:10][CH:11]3[O:13][CH:7]([CH2:6][N:5]([CH2:4][CH2:3][NH:2][S:34]([C:28]4[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=4[F:26])(=[O:36])=[O:35])[CH2:12]3)[CH2:8]2)=[C:18]([F:25])[CH:19]=1)#[N:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 68521326HCID 68521326, compound

Product 1

HCID 68522068HCID 68522068, compoundYield 56.5%

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}-3-fluoro-benzonitrile hydrochloride salt (0.266 g, 0.6 mmol; prep N above) and 2,4-difluorobenzenesulfonyl chloride (0.170 g, 0.80 mmol) were dissolved in DCM (6 mL). Triethylamine (0.416 mL, 3 mmol) was added and the reaction mixture was stirred at room temperature for 20 h under a nitrogen atmosphere. The reaction mixture was concentrated and then redissolved in DCM (3 mL) and transferred to a phase separator. The DCM layer was washed with water (3 mL) and the layers were separated. The retained water was extracted with DCM (3 mL) and the layers were separated. The combined DCM fractions were concentrated under reduced pressure. The crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 173 mg (56%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in DCM (3 mL)
  3. washThe DCM layer was washed with water (3 mL)
  4. customthe layers were separated
  5. extractionThe retained water was extracted with DCM (3 mL)
  6. customthe layers were separated
  7. concentrationThe combined DCM fractions were concentrated under reduced pressure
  8. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-dccf6c5e009d4f008f283b47ddd8d133
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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