Sodium Hydroxide → HCID 67002710, compound

HRID 2362640Notes

Reaction equation

HRID 2362640 reaction equation
[Cl:1][C:2]1[C:3]([C:30]2[S:34][C:33]([C:35]3([OH:39])[CH2:38][CH2:37][CH2:36]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[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:30]2[S:34][C:33]([C:35]3([OH:39])[CH2:38][CH2:37][CH2:36]3)=[N:32][CH:31]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:18][CH:19]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67003553HCID 67003553, compound

Product 1

HCID 67002710HCID 67002710, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(5-chloro-4-(2-(1-hydroxycyclobutyl)thiazol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)benzoic acid (Example 16B) (450 mg, 0.776 mmol) in methanol (7.8 mL) and 2N sodium hydroxide solution (2.7 mL, 5.43 mmol) was heated by microwave irradiation (Biotage, Initiator) in a sealed vessel to 105° C. for 7 minutes. The reaction was cooled to room temperature and concentrated to dryness. The residue was suspended in water, and the pH adjusted to ˜2 with 10% aqueous HCl solution. The solid was filtered and air-dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.69 (bs, 1H), 8.37 (s, 1H), 8.28 (s, 1H), 8.09 (d, J=8.4 Hz, 2H), 7.98 (d, J=8.4 Hz, 2H), 7.19 (s, 1H), 6.68 (s, 1H), 2.70-2.58 (m, 2H), 2.47-2.35 (m, 1H), 2.15-1.82 (m, 2H); MS ESI(+) m/z 425.9 [M+H]+.

Workup

  1. concentrationconcentrated to dryness
  2. filtrationThe solid was filtered
  3. customair-dried

Sources & evidence

ORD record
ord-9f6d76d584674a75b1be8a0361010775
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…