Hydrochloric Acid → HCID 58101291, compound

HRID 237323Notes

Reaction equation

HRID 237323 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]([C:17]3([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[CH2:20][CH2:19][CH2:18]3)[N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.C(N(CC)CC)C.[CH2:42]([S:45](Cl)(=[O:47])=[O:46])[CH2:43][CH3:44].Cl>N1C=CC=CC=1.ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:17]2([CH:15]3[C:16]4[N:4]([CH2:3][CH2:2][NH:1][S:45]([CH2:42][CH2:43][CH3:44])(=[O:47])=[O:46])[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[C:11]=4[CH2:12][CH2:13][NH:14]3)[CH2:20][CH2:19][CH2:18]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 58101268HCID 58101268, compound

Product 1

HCID 58101291HCID 58101291, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 9-(2-aminoethyl)-1-[1-(4-chlorophenyl)cyclobutyl]-1,3,4,9-tetrahydro-2H-b-carboline-2-carboxylate (90 mg, 0.187 mmol) was dissolved in pyridine (2 mL). Triethylamine (38 mg, 0.375 mmol) followed by propane-1-sulfonyl chloride (40 mg, 0.280 mmol) were added. The reaction mixture was stirred over night. The solvent was evaporated in vacuo. The residue was treated with dichloromethane (10 mL) and washed successively with saturated ammonium chloride solution (2×10 mL) and water (10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude intermediate was purified by flash chromatography (silica, dichloromethane, methanol). The obtained compound (58 mg, 0.099 mmol) was dissolved in dichloromethane (2 mL) and excess 5M isopropanolic hydrochloric acid was added. The reaction mixture was stirred over night at room temperature. The solvent was evaporated in vacuo. Yield: 35 mg (0.067 mmol, 68%).

Workup

  1. additionwere added
  2. customThe solvent was evaporated in vacuo
  3. additionThe residue was treated with dichloromethane (10 mL)
  4. washwashed successively with saturated ammonium chloride solution (2×10 mL) and water (10 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude intermediate was purified by flash chromatography (silica, dichloromethane, methanol)
  8. stirringThe reaction mixture was stirred over night at room temperature
  9. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-da3174adcf974b1bb9fda1020fb08a81
Source dataset
uspto-grants-2014_02
Patent number
US08642587B2

Reaction notes

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