Sodium borohydride → HCID 178509285, compound

HRID 407365Notes

Reaction equation

HRID 407365 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][NH:13][C:14]=1[N:15]=[CH:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1.[BH4-].[Na+]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:22])=[N:12][NH:13][C:14]=1[NH:15][CH2:16][C:17]1[NH:21][CH:20]=[CH:19][N:18]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 178509284HCID 178509284, compound

Product 1

HCID 178509285HCID 178509285, compoundYield 91.8%

Procedure

A mixture of 4-benzothiazol-2-yl-N5-(1H-imidazol-2-ylmethylene)-1H-pyrazole-3,5-diamine (13 mg, 0.042 mmol) and NaBH4 (10 mg) was stirred at room temperature for 3 hrs. The solvent was then evaporated and the residue was purified by flash column chromatography eluting with a gradient of CH2Cl2 to CH2Cl2:MeOH=4:1 to yield 12 mg (84%) of the title compound. MS (m/z, ES+): 312.1 (M+1, 80%), 232.1 (100%).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was purified by flash column chromatography
  3. washeluting with a gradient of CH2Cl2 to CH2Cl2

Sources & evidence

ORD record
ord-b340ba24bce7440788c384849f12640d
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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