Pyrrolidine → HCID 22283346, compound

HRID 2308471Notes

Reaction equation

HRID 2308471 reaction equation
Cl[C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[S:10][C:11]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=3[N:13]=2)=[O:7])=[CH:4][N:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>O1CCOCC1>[CH3:25][O:24][C:14]1[C:12]2[N:13]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:26]=[CH:27][C:2]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[N:3][CH:4]=3)[S:10][C:11]=2[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22283272HCID 22283272, compound

Product 1

HCID 22283346HCID 22283346, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-nicotinamide (297 mg, 0.75 mmol) in dioxane (10 ml) was added pyrrolidine (266 mg, 3.7 mmol, 5 eq.) and the mixture stirred at 100° C. for 2 h. After cooling the solvent was evaporated and the residue suspended in methanol (20 ml) at r.t., the solid was then filtered, washed with methanol and finally dried under vacuum (0.05 mmHg, 60° C.) to obtain the title compound as a white solid (230 mg, 71% yield), MS: m/e=431.4 (M+H+).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. customsuspended in methanol (20 ml) at r.t.
  4. filtrationthe solid was then filtered
  5. washwashed with methanol
  6. customfinally dried under vacuum (0.05 mmHg, 60° C.)

Sources & evidence

ORD record
ord-07369cb67d83445a8e4a1dd033afb50e
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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