Sodium Hydroxide → 2-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylic acid

HRID 1426157Notes

Reaction equation

HRID 1426157 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([O:28]C)=[O:27])=[CH:21][N:20]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:19]3[C:24]([N:25]=2)=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][N:20]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59225690Methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate

Product 1

HCID 592256482-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylic acidYield 103%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10 mL round-bottomed flask was charged with methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate (80 mg, 0.17 mmol) and EtOH (3 mL). Sodium hydroxide (0.51 ml, 0.51 mmol) was added and stirred overnight. The methanol was removed and the residue was partitioned between methylene chloride and 0.5 N HCl. Solid K2CO3 was added to adjust to pH 5 and additional methanol was added. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to afford the title compound (80 mg, 103% yield) as an off-white solid. 1H NMR (DMSO-d6) δ 11.0 (bs, 1H), 8.85 (d, 1H), 8.26 (d, 1H), 8.10 (d, 1H), 7.75 (d, 1H), 7.61 (d, 2H), 7.42 (t, 2H), 7.36 (m, 1H), 5.33 (s, 2H). Mass spectrum (apci) m/z=457.1 (M+H).

Workup

  1. customThe methanol was removed
  2. customthe residue was partitioned between methylene chloride and 0.5 N HCl
  3. additionSolid K2CO3 was added
  4. additionwas added
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70d4c2ee48854a2b8ef080e1fdbadc4e
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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