Pyrrolidine → HCID 178434640, compound

HRID 2261695Notes

Reaction equation

HRID 2261695 reaction equation
Br[CH2:2][C:3]1[CH:18]=[CH:17][C:6]2[N:7]=[C:8]([C:10]3[C:14]([CH3:15])=[N:13][NH:12][C:11]=3[NH2:16])[S:9][C:5]=2[CH:4]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[CH3:15][C:14]1[C:10]([C:8]2[S:9][C:5]3[CH:4]=[C:3]([CH2:2][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:18]=[CH:17][C:6]=3[N:7]=2)=[C:11]([NH2:16])[NH:12][N:13]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178434639HCID 178434639, compound

Product 1

HCID 178434640HCID 178434640, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-(6-bromomethylbenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine (20 mg) in ethanol (1 mL) was added excess pyrrolidine. The reaction mixture was stirred at room temperature overnight. The solvent was then removed by evaporation and the residue was purified by flash column chromatography eluting with CHCl3:MeOH=9:1 to yield 2.7 mg of the title compound as a cream coloured solid. MS (m/z, ES+): 314.1 (M+1, 45%), 243.0 (M-C4H8N, 100%).

Workup

  1. customThe solvent was then removed by evaporation
  2. customthe residue was purified by flash column chromatography
  3. washeluting with CHCl3

Sources & evidence

ORD record
ord-6e414f85f88c47b994c81f7ed6261f1b
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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