Pyrrolidine → HCID 178434640, compound

HRID 57298Notes

Reaction equation

HRID 57298 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-296750bdc2fd4abe85d84bc1832718d2
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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