Sodium Hydroxide → HCID 54673430, compound

HRID 2362628Notes

Reaction equation

HRID 2362628 reaction equation
[Cl:1][C:2]1[C:3]([C:33]2[S:37][C:36]([C:38]3([OH:42])[CH2:41][CH2:40][CH2:39]3)=[N:35][CH:34]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:13][CH:12]=3)[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:3]([C:33]2[S:37][C:36]([C:38]3([OH:42])[CH2:41][CH2:40][CH2:39]3)=[N:35][CH:34]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([CH2:17][N:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)=[CH:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67003874HCID 67003874, compound

Product 1

HCID 54673430HCID 54673430, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(5-(5-chloro-2-(4-(pyrrolidin-1-ylmethyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)cyclobutanol (Example 8C) (1.81 g, 2.92 mmol) in methanol (19.49 mL) and aqueous 2N sodium hydroxide (5.85 ml, 11.69 mmol) was heated to 70° C. for 1 hour. The methanol was removed under reduced pressure, and the remaining aqueous layer was diluted with 20 mL water. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with a 2:1 methanol:water solution to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.55 (s, 1H), 8.32 (s, 1H), 8.26 (s, 1H), 7.98-7.91 (m, 2H), 7.43-7.36 (m, 2H), 7.03 (s, 1H), 6.67 (s, 1H), 3.60 (s, 2H), 2.69-2.55 (m, 2H), 2.47-2.33 (m, 6H), 2.04-1.89 (m, 2H), 1.75-1.66 (m, 4H); MS ESI(+) m/z 465.2 [M+H]+.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe remaining aqueous layer was diluted with 20 mL water
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with a 2:1 methanol

Sources & evidence

ORD record
ord-f87ef464853c48a5bc5d84b351f16751
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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