Sodium borohydride → HCID 59333317, compound

HRID 1893463Notes

Reaction equation

HRID 1893463 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:20]([CH:23]=[O:24])=[CH:21][N:22]=2)[C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2.[BH4-].[Na+]>CO.O>[OH:24][CH2:23][C:20]1[N:8]2[C:9]3[C:14]([N:15]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])[C:7]2=[N:22][CH:21]=1)=[CH:13][C:12]([C:16]([F:17])([F:19])[F:18])=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 25120537HCID 25120537, compound

Product 1

HCID 59333317HCID 59333317, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline-1-carbaldehyde prepared as in example 36 (8 mg, 0.024 mmol) in anhydrous methanol (300 μL), cooled at 0° C. was added sodium borohydride (2 mg, 0.047 mmol). The mixture was allowed to warm to room temperature over 1 h under argon and then diluted with water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 9/1) to afford the title compound as a white solid (5 mg, 61%).

Workup

  1. temperatureto warm to room temperature over 1 h under argon
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 9/1)

Sources & evidence

ORD record
ord-b779f65da13f4cc3b3bb7319c72d9781
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…