Cyanamide → HCID 10323136, compound

HRID 2415269Notes

Reaction equation

HRID 2415269 reaction equation
[N:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)=[C:2]=[S:3].[N:18]#[C:19][NH2:20].CC(C)([O-:24])C.[K+].Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)=[O:30]>C(#N)C.O>[C:7]([OH:24])(=[O:8])[CH3:16].[NH2:18][C:19]1[N:20]=[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][N:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)=[CH:16][CH:17]=2)[S:3][C:28]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)=[O:30]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 27374513-Fluorophenacyl bromideHCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 10323136HCID 10323136, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-[2-(4-Isothiocyanato-phenoxy)-ethyl]-pyrrolidine (50 mg, 0.2 mmol) (from Example 5) and cyanamide (9.2 mg, 0.22 mmol) in acetonitrile (2 mL). Potassium t-butoxide solution (2 mL, 0.1M in tert-butanol, 0.2 mmol) was added and the solution stirred for 1 hour. 2-Bromo-1-(3-fluoro-phenyl)ethanone (44 mg, 2 mmol) (Maybridge Chemical.) was added and the solution was stirred at room temperature for 4 hours, poured into water, stirred for 1 hour, extracted with ethyl acetate, dried (Na2SO4) and concentrated to a solid. The crude product was purified by HPLC using a Waters Symmetry C-18 2×10 cm column with the following gradient: A (0.1% acetic acid in water), B (acetonitrile), A to B gradient (10 to 75% over 10 minutes), flow rate: 20 mL/minute. Mass spectrum (ES) MH+=427.

Workup

  1. stirringthe solution was stirred at room temperature for 4 hours
  2. stirringstirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a solid
  6. customThe crude product was purified by HPLC
  7. customto B gradient (10 to 75% over 10 minutes), flow rate: 20 mL/minute

Sources & evidence

ORD record
ord-975bf085df7c4927bd43bc2071ad9dc2
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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