Methanol → HCID 178517345, compound

HRID 80245Notes

Reaction equation

HRID 80245 reaction equation
Cl.O1CCOCC1.[S:8]1[C:12]2[CH:13]=[C:14]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[C:24]5[N:30]=[CH:29][N:28](OCC[Si](C)(C)C)[C:25]5=[N:26][CH:27]=4)[C:18]3=[O:38])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1.CO>C(Cl)Cl>[S:8]1[C:12]2[CH:13]=[C:14]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[C:24]5[N:30]=[CH:29][NH:28][C:25]5=[N:26][CH:27]=4)[C:18]3=[O:38])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 596362291-benzothiazol-6-yl-3-[3-(2-trimethylsilanyl-ethoxy)-3H-imidazo[4,5-b]pyridin-6-yl]-imidazolidin-2-one

Product 1

HCID 178517345HCID 178517345, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,4-Dioxane HCl (5 ml) was added to 1-benzothiazol-6-yl-3-[3-(2-trimethylsilanyl-ethoxy)-3H-imidazo[4,5-b]pyridin-6-yl]-imidazolidin-2-one (I-183b: 100 mg, 0.2145 mmol) and the resulting mixture was stirred room temperature for 6 hours. The reaction was monitored by TLC (10% MeOH in DCM). The reaction mixture was concentrated and washed with diethyl ether. Purification by preparative HPLC afforded 20 mg of the product (25.4% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-8f9985ba741d4e2ab9d16ba8b0551b8c
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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