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

HRID 571895노트

반응식

HRID 571895 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-24697ea9225244b28ff4a074210eb808
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029356B2

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