N-Iodosuccinimide → HCID 86654729, compound

HRID 2092839Notes

Reaction equation

HRID 2092839 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([NH:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[N:8][C:9]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][C:5]=2[CH2:4][NH:3]1.[I:34]N1C(=O)CCC1=O>C(Cl)Cl>[I:34][C:10]1[C:5]2[CH2:4][NH:3][C:2](=[O:1])[C:6]=2[C:7]([NH:26][C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)=[N:8][C:9]=1[NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86654728HCID 86654728, compound

Product 1

HCID 86654729HCID 86654729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a screw-top vial was added tert-butyl (1S,2R)-2-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (73 mg, 0.162 mmol) and 1-iodopyrrolidine-2,5-dione (36.4 mg, 0.162 mmol) in DCM (1.6 mL) to give a yellow solution. The reaction was stirred 0.5 h at RT. The reaction mixture was diluted with DCM (10 mL) and washed with saturated aq NaHCO3 (10 mL), water (10 mL), and brine (10 mL). The collected organic layers were dried with sodium sulfate and concentrated to give the title compound as a brown solid, which was used without further purification (85.7 mg, 92%). [M+H] calc'd for C25H32IN5O3, 578. found, 578.

Workup

  1. customto give a yellow solution
  2. washwashed with saturated aq NaHCO3 (10 mL), water (10 mL), and brine (10 mL)
  3. dry with materialThe collected organic layers were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-21013047037f4cb0887726f6f07ea10b
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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