Pyrrolidine → HCID 68328870, compound

HRID 634183Notes

Reaction equation

HRID 634183 reaction equation
Br[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:11]=[C:10]3[C:26]2[CH:31]=[N:30][CH:29]=[C:28]([CH:32]3[CH2:34][CH2:33]3)[N:27]=2)=[N:5][N:6]=1.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>CN1C(=O)CCC1.C(Cl)Cl>[CH:32]1([C:28]2[N:27]=[C:26]([C:10]3[C:9]4[C:13](=[CH:14][CH:15]=[C:7]([C:4]5[O:3][C:2]([N:35]6[CH2:39][CH2:38][CH2:37][CH2:36]6)=[N:6][N:5]=5)[CH:8]=4)[N:12]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:11]=3)[CH:31]=[N:30][CH:29]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 683288112-bromo-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole

Product 1

HCID 68328870HCID 68328870, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A brown-orange solution of 2-bromo-5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazole (35.0 mg, 0.065 mmol) and pyrrolidine (16.2 μL, 0.195 mmol) in NMP (1.0 mL) was heated in a sealed microwave process vial under argon at 120° C. for 18 h. The mixture was then diluted with DCM (5 mL), concentrated onto silica gel, and chromatographically purified (silica gel, 0-10% MeOH/DCM) to provide 2-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-5-(pyrrolidin-1-yl)-1,3,4-oxadiazole (22.7 mg, 0.043 mmol, 66%) as a yellow oil: MS (ESI, pos. ion) m/z: 527.2 (M+1).

Workup

  1. concentrationconcentrated onto silica gel
  2. customchromatographically purified (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-2ef33ac5989840bd843c8b9beb39362d
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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