Hydrochloric Acid → HCID 54674685, compound

HRID 2362709Notes

Reaction equation

HRID 2362709 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[N:30](S(C2C=CC(C)=CC=2)(=O)=O)[C:15]2=[N:16][CH:17]=[CH:18][C:19]([C:20]3[S:24][C:23]([C:25]4([OH:29])[CH2:28][CH2:27][CH2:26]4)=[N:22][CH:21]=3)=[C:14]2[CH:13]=1.Cl>CO.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[NH:30][C:15]2=[N:16][CH:17]=[CH:18][C:19]([C:20]3[S:24][C:23]([C:25]4([OH:29])[CH2:28][CH2:27][CH2:26]4)=[N:22][CH:21]=3)=[C:14]2[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67003746HCID 67003746, compound

Product 1

HCID 54674685HCID 54674685, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(5-(2-(5-fluoro-1-methyl-1H-indol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 107D) in methanol (2.0 mL) and 2N sodium hydroxide solution (700 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 trifluoroacetic acid and B is acetonitrile) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.14 (s, 1H), 8.54 (s, 1H), 8.16 (d, J=5.2 Hz, 1H), 8.09 (s, 1H), 7.87 (d of d, J=10.08 & 2.4 Hz, 1H), 7.58 (d of d, J=8.95 & 4.5 Hz, 1H), 7.27 (d, J=5.2 Hz, 1H), 7.14 (t, 1H), 6.99 (s, 1H), 3.88 (s, 3H), 2.64-2.55 (m, 2H), 2.45-2.35 (m, 2H), 2.05-1.92 (m, 2H); MS ESI(+) m/z 419.5 [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-5ed5bb4bc7d8401d8d5b70c087b9c8c6
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…