N-Iodosuccinimide → HCID 58180567, compound

HRID 220379Notes

Reaction equation

HRID 220379 reaction equation
[CH:1]1([N:4]([CH:33]2[CH2:35][CH2:34]2)[C:5]([C:7]2[N:30]([CH2:31][CH3:32])[C:10]3=[N:11][C:12]([NH:19][C:20]([NH:22][C:23]4[N:27]([CH3:28])[N:26]=[C:25]([CH3:29])[CH:24]=4)=[S:21])=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C1C(=O)N(I)C(=O)C1>C(Cl)(Cl)Cl>[CH:1]1([N:4]([CH:33]2[CH2:35][CH2:34]2)[C:5]([C:7]2[N:30]([CH2:31][CH3:32])[C:10]3=[N:11][C:12]([NH:19][C:20]4[S:21][C:24]5[C:25]([CH3:29])=[N:26][N:27]([CH3:28])[C:23]=5[N:22]=4)=[C:13]4[N:17]=[CH:16][N:15]([CH3:18])[C:14]4=[C:9]3[CH:8]=2)=[O:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58180565HCID 58180565, compound

Product 1

HCID 58180567HCID 58180567, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dicyclopropyl-4-(3-(1,3-dimethyl-1H-pyrazol-5-yl)thioureido)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 41B, 41 mg, 0.083 mmol) was dissolved in chloroform (2780 μL) and cooled to 0° C. NIS (18.76 mg, 0.083 mmol) was slowly added and the reaction was warmed to room temperature. The reaction mixture was concentrated. Methanol and ether were added and the mixture was filtered. After standing for a week, product precipitated out of the solution. The product was triturated with methanol. N,N-Dicyclopropyl-4-(1,3-dimethyl-1H-pyrazolo[3,4-d]thiazol-5-ylamino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide was isolated as a pale yellow solid (8.1 mg, 20% yield).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. additionMethanol and ether were added
  4. filtrationthe mixture was filtered
  5. waitAfter standing for a week
  6. customproduct precipitated out of the solution
  7. customThe product was triturated with methanol

Sources & evidence

ORD record
ord-143d632151fa454caad110cc55c0c349
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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