Diisobutylaluminum hydride → HCID 57742587, compound

HRID 335209Notes

Reaction equation

HRID 335209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[N:17]([CH3:25])[C:18]([C:21](OC)=[O:22])=[CH:19][N:20]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C>C1COCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[N:17]([CH3:25])[C:18]([CH2:21][OH:22])=[CH:19][N:20]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydride2×HCID 86631518HCID 86631518, compound

Product 1

HCID 57742587HCID 57742587, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 9357Potassium Sodium TartrateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-(5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)-1-methyl-1H-imidazole-5-carboxylate (0.076 g, 0.17 mmol) dissolved in THF (5 mL) was cooled to 0° C. DIBAL-H (1M in hexanes, 0.52 mL, 0.52 mmol) was added. After 15 minutes, DIBAL-H (0.52 mL, 0.52 mmol) was added again. The solution was diluted with a saturated solution of Rochelle's Salt (10 mL) and the solution stirred overnight. The material was extracted with dichloromethane and the organic layer was dried, and concentrated. Reverse phase HPLC purification gave the title compound (0.006 g, 9% yield) as a white solid. 1H NMR (DMSO-d6) δ 2.18 (s, 3H), 3.64 (s, 3H), 4.50 (d, 2H), 5.22 (t, 1H), 5.75 (s, 1H), 6.38 (bs, 1H), 7.11 (s, 1H), 8.22 (bs, 1H).

Workup

  1. extractionThe material was extracted with dichloromethane
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-1275909a023147acb81ea5ba6074dff6
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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