N-Iodosuccinimide → HCID 86654729, compound

HRID 711536Notes

Reaction equation

HRID 711536 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-3437837dbe0b4cf695a4c7cbb2910403
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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