HCID 90094063, compound → HCID 90092825, compound

HRID 1753041Notes

Reaction equation

HRID 1753041 reaction equation
C(=[N:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[C:27]3[CH:28]=[N:29][CH:30]=[C:31]([F:32])[C:26]=3[N:25]([C:33]([CH3:44])([CH3:43])[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH:24]=2)=[O:22])[CH:18]=[N:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[NH2:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[C:27]3[CH:28]=[N:29][CH:30]=[C:31]([F:32])[C:26]=3[N:25]([C:33]([CH3:44])([CH3:43])[CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[CH:24]=2)=[O:22])[CH:18]=[N:19][CH:20]=1

Participants

4

Reactant 1

HCID 90094063HCID 90094063, compound

Product 1

HCID 90092825HCID 90092825, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(benzhydrylidene-amino)-pyridin-3-yl]-{1-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-7-fluoro-1H-pyrrolo[3,2-c]pyridin-3-yl}-methanone (Preparation 36, 1 g, 1.65 mmol) in THF (80 mL), citric acid (30 mL, 1 M) was added at room temperature and stirred for 4 hours, then quenched with saturated sodium bicarbonate solution and was extracted with ethyl acetate. The organic phase was dried over sodium sulphate, evaporated in vacuo to afford the crude compound, purified by column chromatography over alumina (gradient of DCM: Methanol 98:2 to 97:3) to afford the title compound as a pale yellow solid (69%, 500 mg).

Workup

  1. customquenched with saturated sodium bicarbonate solution
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated in vacuo
  5. customto afford the crude compound
  6. custompurified by column chromatography over alumina (gradient of DCM: Methanol 98:2 to 97:3)

Sources & evidence

ORD record
ord-582b8b730e5344698a4b526ceb061feb
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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