Hydrochloric Acid → N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

HRID 331017Notes

Reaction equation

HRID 331017 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]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[N:13]([CH:30]3[CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31]3)[CH:12]=1)[N:7]([CH3:41])[CH2:6][CH2:5]2.Cl.O1CCOCC1>C(Cl)Cl>[NH:32]1[CH2:31][CH:30]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([NH:20][S:21]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)(=[O:23])=[O:22])=[C:19]3[C:11]([C:10]3[CH:9]=[C:8]4[C:4]([CH2:5][CH2:6][N:7]4[CH3:41])=[CH:3][C:2]=3[F:1])=[CH:12]2)[CH2:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86720287tert-butyl 3-(3-(5-fluoro-1-methylindolin-6-yl)-4-(phenylsulfonamido)-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate

Product 1

HCID 71090140N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(3-(5-fluoro-1-methylindolin-6-yl)-4-(phenylsulfonamido)-1H-pyrrolo[2,3-b]pyridin-1-yl)azetidine-1-carboxylate (D33) (489 mg, 0.847 mmol) in DCM (8 mL) was added 4M HCl in dioxane (4.23 mL, 16.93 mmol). The final mixture was stirred at RT for 6 hours. The mixture was concentrated in vacuo. The residue was dissolved in MeOH and passed through a SCX cartridge eluting with MeOH followed by 2M ammonia in MeOH to give the title compound (394 mg). LCMS (A): m/z (M+H)+ 478, C25H24FN5O2S requires 477 (acidic).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. washeluting with MeOH

Sources & evidence

ORD record
ord-fa3208f4243a4f329eb74e3a932cccbb
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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