Pyrrolidine → HCID 22283346, compound

HRID 2250705Notes

Reaction equation

HRID 2250705 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-a8cca2bc52464f9ab52dfc92bea05d7b
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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