Hydrochloric Acid → 1-(5-(5-fluoro-2-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol

HRID 2362698Notes

Reaction equation

HRID 2362698 reaction equation
[F:1][C:2]1[C:3]([C:31]2[S:35][C:34]([C:36]3([OH:40])[CH2:39][CH2:38][CH2:37]3)=[N:33][CH:32]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=3)[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.Cl>CO.[OH-].[Na+]>[F:1][C:2]1[C:3]([C:31]2[S:35][C:34]([C:36]3([OH:40])[CH2:39][CH2:38][CH2:37]3)=[N:33][CH:32]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 670028911-(5-(5-fluoro-2-(3-(methylsulfonyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol

Product 1

HCID 546745241-(5-(5-fluoro-2-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(5-(5-fluoro-2-(3-(methylsulfonyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 91A) (94.2 mg, 0.158 mmol) in methanol (2.500 mL) and 2N sodium hydroxide solution (833 μL) was heated by microwave irradiation (Biotage, Initiator) to 120° C. for 30 minutes. The reaction was cooled to room temperature, and the pH adjusted to ˜3 with 10% aqueous HCl solution. The resulting solution was purified by reverse phase high performance liquid chromatography (RP HPLC, eluting with a gradient of 5% B in A to 75% B in A over 25 minutes, wherein A is water containing 0.1% v/v ammonium acetate and B is acetonitrile) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.73 (b s, 1H), 8.60 (b s, 1H), 8.57 (s, 1H), 8.39 (d, J=8.85 Hz, 1H), 8.38 (d, J=3.51 Hz, 1H), 7.91 (d, J=7.78 Hz, 1H), 7.78 (t, 1H), 7.56 (s, 1H), 3.33 (s, 3H), 2.64-2.59 (m, 2H), 2.45-2.37 (m, 2H), 2.03-1.93 (m, 2H); MS ESI(+) m/z 443.9 [M+H]+.

Workup

  1. customThe resulting solution was purified by reverse phase high performance liquid chromatography (RP HPLC
  2. washeluting with a gradient of 5% B in A to 75% B in A over 25 minutes

Sources & evidence

ORD record
ord-89ad90bad1a0435a9534e910b91213f7
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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