N-Iodosuccinimide → HCID 69545705, compound

HRID 1016463Notes

Reaction equation

HRID 1016463 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:8][CH2:9][NH:10][C:11]1[N:16]2[N:17]=[C:18]([CH3:20])[CH:19]=[C:15]2[N:14]=[C:13]([CH3:21])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[I:28]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:27])[N:7]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:8][CH2:9][NH:10][C:11]1[N:16]2[N:17]=[C:18]([CH3:20])[C:19]([I:28])=[C:15]2[N:14]=[C:13]([CH3:21])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 69545994HCID 69545994, compound

Product 1

HCID 69545705HCID 69545705, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 0° C. stirred solution of cyclopentyl-[2-(2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ylamino)-ethyl]-carbamic acid tert-butyl ester (89 mg, 0.24 mmol) in chloroform (5 mL) was added N-iodosuccinimide (54 mg, 0.24 mmol). After stirring 30 minutes the reaction was extracted from saturated aqueous sodium thiosulfate with chloroform. The combined extracts were dried (Na2SO4), concentrated under reduced pressure to give the product as a slightly yellowed glass (102 mg, 85%): +APcI MS (M+1)+ 500; 1H NMR (CDCl3) δ: 5.82 (s, 1H), 4.25-4.10 (br s, 1H), 3.46 (s, 4H), 2.51 (s, 3H), 2.41 (s, 3H), 1.50 (s, 9H).

Workup

  1. extractionwas extracted from saturated aqueous sodium thiosulfate with chloroform
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e778974f539d439daf412bcfb25e5be2
Source dataset
uspto-grants-2002_11
Patent number
US06476038B1

Reaction notes

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