Hydrochloric Acid → HCID 59161276, compound

HRID 545548Notes

Reaction equation

HRID 545548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[C:10]1[CH2:9][CH2:8][CH:7]([NH2:23])[CH2:6][C:5]2=1.Cl.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28].C(N(CC)CC)C>CN1CCCC1=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)[C:10]1[CH2:9][CH2:8][CH:7]([NH:23][C:27](=[O:28])[N:26]([CH3:30])[CH3:25])[CH2:6][C:5]2=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl Chloride2×HCID 8471TriethylamineHCID 57431667HCID 57431667, compound

Product 1

HCID 59161276HCID 59161276, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Mix 6-bromo-9-(3-fluoro-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-ylamine.HCl (Preparation 51) (200 mg, 0.49 mmol), N,N-dimethylcarbamoyl chloride (54 μL, 63 mg, 0.59 mmol), triethylamine (205 μL, 149 mg, 1.47 mmol), CH2Cl2 (6 mL), and N-methylpyrrolidinone (2 mL). Stir at room temperature for 18 h, then add more N,N-dimethylcarbamoyl chloride (54 μL, 63 mg, 0.59 mmol). Stir at room temperature for 60 h, then evaporate the solvents. Dilute the residue with EtOAc (80 mL) and wash the organic solution with HCl (<1N in water, 40 mL) and aqueous NaHCO3. Dry (MgSO4), filter, and concentrate the organic portion to obtain 308 mg crude product as a brown oil. Purify on silica gel (12 g), eluting with 80-100% EtOAc/hexanes to afford 164 mg (75%) of the title compound as a white foam. MS (ES): 444, 446 (M+1); HPLC: Rt=3.27 min, (92%).

Workup

  1. stirringStir at room temperature for 60 h
  2. customevaporate the solvents
  3. additionDilute the residue with EtOAc (80 mL)
  4. washwash the organic solution with HCl (<1N in water, 40 mL) and aqueous NaHCO3
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate the organic portion
  8. customto obtain 308 mg crude product as a brown oil
  9. customPurify on silica gel (12 g)
  10. washeluting with 80-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-0389bf1e8ca8499aa7c22201807f6b62
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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