Sodium Hydroxide → HCID 22040478, compound

HRID 2070335Notes

Reaction equation

HRID 2070335 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].F[C:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:12][CH:11]=[C:10]([N+:21]([O-])=O)[C:9]=1[NH2:24].[BH4-].[Na+].[OH-].[Na+]>O.C1COCC1>[CH:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:13]3[CH:8]=[C:9]([NH2:24])[C:10]([NH2:21])=[CH:11][CH:12]=3)[CH2:15][CH2:16]2)[CH2:10][CH2:9][CH2:8][CH2:13]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21226445Aluminium lithium hydrideHCID 220408162-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

Product 1

HCID 22040478HCID 22040478, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A flame dried 500 mL three necked round bottom flask purged with N2 was charged with LAH (3.0 g, 75.0 mmol) and dry THF (240 mL). The resulting suspension was cooled to 0° C. and t-butyl ester 1 (20.7 g, 60 mmol) was slowly added while keeping the internal reaction temperature under 5° C. Reaction stirred at 0° C. for 2 hr followed by stirring at RT for overnight. NaBH4 (2.27 g, 60 mmol) was added and stirred for an additional hour at rt. After the reaction was judged complete, the stirred reduction mixture was treated with successive dropwise addition of 3 mL H2O, 3 mL NaOH, and 9 mL H2O. Reaction mixture filtered through Celite, washed with ethyl acetate and methanol, and evaporated. Crude product absorbed onto silica gel and chromatographed using 97:3 CH2Cl2/MeOH to give 2 as an orange solid. 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=5.5 Hz, 1H), 8.05 (br s, 1H), 7.96 (d, J=2.75 Hz, 1H), 7.29 (d, J=2.75 Hz, 1H), 6.92 (d, J=9.35 Hz, 1H), 6.75 (m, 2H), 4.68 (s, 2H), 3.07 (d, J=5.23 Hz, 3H).

Workup

  1. dry with materialA flame dried 500 mL three necked round bottom flask
  2. custompurged with N2
  3. customunder 5° C
  4. customReaction
  5. stirringby stirring at RT for overnight
  6. stirringstirred for an additional hour at rt
  7. customReaction mixture
  8. filtrationfiltered through Celite
  9. washwashed with ethyl acetate and methanol
  10. customevaporated
  11. customCrude product absorbed onto silica gel
  12. customchromatographed

Sources & evidence

ORD record
ord-fff55051e4554774b09f964d710d35fb
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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