HCID 131733649, compound → HCID 73672464, compound

HRID 1753001Notes

Reaction equation

HRID 1753001 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[C:13]([C:20]([C:22]2[CH:23]=[C:24]([NH:28][C:29](=[O:38])[CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=3)[CH:25]=[N:26][CH:27]=2)=[O:21])=[CH:12]1)([CH3:10])[CH3:9])(C)(C)C>C1COCC1.Cl.O1CCOCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][C:29]([NH:28][C:24]2[CH:25]=[N:26][CH:27]=[C:22]([C:20]([C:13]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:19]=4[N:11]([C:8]([CH3:10])([CH3:9])[CH2:7][OH:6])[CH:12]=3)=[O:21])[CH:23]=2)=[O:38])=[N:32][CH:33]=1

Participants

4

Reactant 1

HCID 131733649HCID 131733649, compound

Product 1

HCID 73672464HCID 73672464, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

To a solution of N-(5-{1-[2-(tert-Butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-1H-pyrrolo[3,2-c]pyridine-3-carbonyl}-pyridin-3-yl)-2-(5-chloro-pyridin-2-yl)-acetamide (Preparation 8, 45 mg, 0.077 mmol) in THF (3 mL), 4M dioxane-HCl (0.4 mL) was added and stirred at room temperature for 18 hours. The reaction was evaporated in vacuo and purified by column chromatography on silica gel (gradient of MeOH: DCM 0:100 to 3:100) to afford the title compound as a yellow solid in 69% yield, 25 mg.

Workup

  1. customThe reaction was evaporated in vacuo
  2. custompurified by column chromatography on silica gel (gradient of MeOH: DCM 0:100 to 3:100)

Sources & evidence

ORD record
ord-19cca79154a747af9a2c77ea3189facf
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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