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

HRID 1186577
Notes
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Reaction equation

HRID 1186577 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344DichloromethaneSolvent
HCID 6422
Trifluoroacetic acid
Solvent

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-a189e4e202684397aa6d1afd4698ee79
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673893B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes