Sodium Hydroxide → 2-(4-(5-fluoro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid

HRID 2362680Notes

Reaction equation

HRID 2362680 reaction equation
[F:1][C:2]1[C:3]([C:32]2[S:36][C:35]([C:37]3([OH:41])[CH2:40][CH2:39][CH2:38]3)=[N:34][CH:33]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]([O:19]CC)=[O:18])[CH:15]=3)[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[C:3]([C:32]2[S:36][C:35]([C:37]3([OH:41])[CH2:38][CH2:39][CH2:40]3)=[N:34][CH:33]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]([OH:19])=[O:18])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67003645ethyl 2-(4-(5-fluoro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 670037172-(4-(5-fluoro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(4-(5-fluoro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-pyrazol-1-yl)acetate (Example 65A) (734 mg, 1.232 mmol) in methanol (8.2 mL) and 2N aqueous sodium hydroxide solution (2.16 mL, 4.31 mmol) was heated by microwave irradiation (Biotage, Initiator) in a sealed vessel to 105° C. for 5 minutes. The reaction was cooled to room temperature and concentrated to a volume of 2 mL. The solution was diluted with 10% aqueous HCl. The solid was filtered and air-dried to give the title compound. MS ESI(+) m/z 413.9 [M+H]+.

Workup

  1. concentrationconcentrated to a volume of 2 mL
  2. additionThe solution was diluted with 10% aqueous HCl
  3. filtrationThe solid was filtered
  4. customair-dried

Sources & evidence

ORD record
ord-42ddfcd3ea29437bbb6654b443e3516b
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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