Hydrochloric Acid → HCID 86646905, compound

HRID 2177104Notes

Reaction equation

HRID 2177104 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH:26][C:27](=O)[CH3:28].CSC.B.[ClH:37].C(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:37].[CH2:27]([NH:26][CH:7]1[CH:6]([CH2:5][C:4]2[CH:30]=[CH:31][CH:32]=[C:2]([F:1])[CH:3]=2)[C:15]2[CH:14]=[C:13]([CH2:16][CH2:17][CH2:18][NH:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8]1)[CH3:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 57471362HCID 57471362, compound

Product 1

HCID 86646905HCID 86646905, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-(1-(3-Fluorobenzyl)-7-(3-(propylsulfonamido)propyl)-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (cf. example 214, 19.5 mg, 0.042 mmol) was dissolved in tetrahydrofuran (1 mL) and borane dimethylsulfide (106 μL, 0.212 mmol) was added. The reaction mixture was stirred for 5 hours at 50° C. After cooling to room temperature aqueous hydrochloric acid was added. The mixture was made alkaline by the addition of sodium bicarbonate and extracted several times with dichloromethane. The combined organic extracts were dried (MgSO4), concentrated in vacuo and the crude product purified by flash-chromatography (silica gel, dichloromethane, methanol). An excess of 1 M hydrochloric acid in ether was added to the purified product and the ether distilled off. Yield: 7 mg (0.016 mmol, 37%).

Workup

  1. additionwas added
  2. extractionextracted several times with dichloromethane
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe crude product purified by flash-chromatography (silica gel, dichloromethane, methanol)
  6. additionAn excess of 1 M hydrochloric acid in ether was added to the purified product
  7. distillationthe ether distilled off

Sources & evidence

ORD record
ord-6644a0d9dc584af59be105a1df746a8c
Source dataset
uspto-grants-2015_06
Patent number
US09067871B2

Reaction notes

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