Hydrochloric Acid → N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidine-4-sulfonamide, hydrochloride

HRID 331023Notes

Reaction equation

HRID 331023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]1[C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[NH:20][S:21]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)(=[O:23])=[O:22])[N:13]([CH:37]([CH3:39])[CH3:38])[CH:12]=1)[N:7]([CH3:40])[CH2:6][CH2:5]2.[ClH:41].O1CCOCC1>C(Cl)Cl>[ClH:41].[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]1[C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[NH:20][S:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)(=[O:23])=[O:22])[N:13]([CH:37]([CH3:38])[CH3:39])[CH:12]=1)[N:7]([CH3:40])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71092026tert-butyl 4-(N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfamoyl)piperidine-1-carboxylate

Product 1

HCID 131731993N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidine-4-sulfonamide, hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(N-(3-(5-fluoro-1-methylindolin-6-yl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfamoyl)piperidine-1-carboxylate (D38) (442 mg, 0.773 mmol) in DCM (5 mL) at RT was added 4M HCl in 1,4-dioxane (1.933 mL, 7.73 mmol). The reaction mixture stirred at RT overnight. The reaction mixture was concentrated in vacuo to afford the title compound (500 mg). The material was used in next step without further purification. LCMS (A): m/z [(M−HCl)+H]+ 472, C24H30FN5O2S.HCl requires 507 (acidic).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-22bd6cba5a804579aea633c53721e0e4
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

Loading…