Sodium borohydride → N-(5-(3,5-Difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

HRID 512940Notes

Reaction equation

HRID 512940 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[C:36]([F:38])[CH:37]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32])=O.[BH4-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[F:38][C:36]1[CH:35]=[C:4]([CH:3]=[C:2]([F:1])[CH:37]=1)[CH2:5][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:34])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)=[CH:20][C:19]=1[N+:31]([O-:33])=[O:32]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 68671073N-(5-(3,5-Difluorobenzoyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamide

Product 1

HCID 25175858N-(5-(3,5-Difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-nitrobenzamideYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

N-[5-(3,5-Difluoro-benzoyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-nitro-benzamide (3.61 g, 6.93 mmol) was dissolved in DCM (150 mL) in argon atmosphere and trifluoroacetic acid (150 mL) is added under stirring. Sodium borohydride pellets (2.62 gr, 69.3 mmol) is gradually added over a period of 72 hours. The reaction mixture was evaporated, taken up with a mixture MeOH/acetone and stirred for 1 hour. The resulting mixture was evaporated to dryness, redissolved in MeOH and NaOH 8N was added till basic pH was reached. Crude was evaporated and ice/water was added, the solid thus formed was filtered, washed with water and dried under vacuum at 80° C. affording 3.22 g of title compound (92% yield).

Workup

  1. additionis added
  2. additionis gradually added over a period of 72 hours
  3. customThe reaction mixture was evaporated
  4. stirringstirred for 1 hour
  5. customThe resulting mixture was evaporated to dryness
  6. dissolutionredissolved in MeOH
  7. additionNaOH 8N was added till basic pH
  8. customCrude was evaporated
  9. additionice/water was added
  10. customthe solid thus formed
  11. filtrationwas filtered
  12. washwashed with water
  13. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-ecf0f1e737d247a6a9842f19b8582a4c
Source dataset
uspto-grants-2015_08
Patent number
US09102662B2

Reaction notes

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