4-Hydroxypyrrolidine → HCID 72948899, compound

HRID 1500941Notes

Reaction equation

HRID 1500941 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:23][CH2:24]Cl)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1.[NH:28]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]1>CC#N>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]2[N:6]([CH2:23][CH2:24][N:28]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 89924199HCID 89924199, compound

Product 1

HCID 72948899HCID 72948899, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-{[5-chloro-1-(2-chloroethyl)-1H-benzimidazol-2-yl]methyl}-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (110 mg, 0.26 mmol) and 3-pyrrolidinol (1 mL) in CH3CN (2 mL) was heated at 150° C. for 1 hour under microwave irradiation. The resulting mixture was concentrated in vacuo and the residue was purified by column chromatography (MeOH:DCM=3:25) to afford the title product as a grey solid (8 mg, yield: 6%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (MeOH:DCM=3:25)

Sources & evidence

ORD record
ord-0fb8ea3790964e5c91d16ae7cc36be92
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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