Pyrrolidine → HCID 15979642, compound

HRID 1678795Notes

Reaction equation

HRID 1678795 reaction equation
Cl[CH2:2][C:3]1[N:15]2[C:6]([C:7]3[CH:8]=[C:9]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:10]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:18][CH:17]=4)=[N:11][C:12]=3[CH:13]=[CH:14]2)=[N:5][N:4]=1.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>CS(C)=O>[C:31]1([C:9]2[C:10]([C:16]3[CH:17]=[CH:18][C:19]([CH2:20][NH2:21])=[CH:29][CH:30]=3)=[N:11][C:12]3[CH:13]=[CH:14][N:15]4[C:3]([CH2:2][N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)=[N:4][N:5]=[C:6]4[C:7]=3[CH:8]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 59472939HCID 59472939, compound

Product 1

HCID 15979642HCID 15979642, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 26-1 (0.05 g, 0.1 mmol) in DMSO (1 ml) was added pyrrolidine. The solution was heated at 150° C. for 30 min. The reaction mixture was purified using reverse phase HPLC. The residue was dissolved in MeOH (0.5 ml) and was treated with 1N HCl (0.4 ml). The reaction mixture was stirred at 35° C. for 1 day. Solvent removal afforded the desired product 26-2 as a solid.

Workup

  1. customThe reaction mixture was purified
  2. dissolutionThe residue was dissolved in MeOH (0.5 ml)
  3. additionwas treated with 1N HCl (0.4 ml)
  4. customSolvent removal

Sources & evidence

ORD record
ord-3bf3d0633c5343ab8ae2077f05dff2f7
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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