Borohydride → HCID 86597482, compound

HRID 860516Notes

Reaction equation

HRID 860516 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[N:10]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:11]=[C:12]([CH3:22])[C:13]=2[C:14](=[O:21])[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:5]=[CH:4][N:3]=1.[BH4-].[Na+].[BH4-]>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]3[N:10]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:11]=[C:12]([CH3:22])[C:13]=2[CH:14]([OH:21])[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 86597483HCID 86597483, compound

Product 1

HCID 86597482HCID 86597482, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[4-(2-chloro-4-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]-5-oxopentanoic acid (47 mg) in EtOH (1 mL) was added sodium borohydride (5 mg) in an ice-water bath under N2. After 10 min, the mixture was stirred at ambient temperature. After 1 h, another odium borohydride (5 mg) was added. After 2 h, the reaction mixture was partitioned between CHCl3 and H2O. The aqueous layer was extracted with CHCl3 twice. The combined organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by p-TLC (CHCl3-MeOH=10-1) to give 5-[4-(2-chloro-4-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]-5-hydroxypentanoic acid as yellow amorphous (28 mg).

Workup

  1. waitAfter 1 h
  2. waitAfter 2 h
  3. customthe reaction mixture was partitioned between CHCl3 and H2O
  4. extractionThe aqueous layer was extracted with CHCl3 twice
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by p-TLC (CHCl3-MeOH=10-1)

Sources & evidence

ORD record
ord-a317f8177667475fbb9fd96e44b821cf
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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