Sodium Bicarbonate → HCID 178516631, compound

HRID 1852492Notes

Reaction equation

HRID 1852492 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:15](=[O:16])[CH2:14][C:13](=[O:17])[NH:12][C:11]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=[CH:25][C:10]2=3)[CH:6]=[CH:7][CH:8]=1)#[N:2].C([Sn]([N:39]=[N+:40]=[N-:41])(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH:39]1[C:1]([C:3]2[CH:4]=[C:5]([N:9]3[C:15](=[O:16])[CH2:14][C:13](=[O:17])[NH:12][C:11]4[C:18]5[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=5[CH:24]=[CH:25][C:10]3=4)[CH:6]=[CH:7][CH:8]=2)=[N:2][N:41]=[N:40]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4984872Tributyltin azideHCID 56603173HCID 56603173, compound

Product 1

HCID 178516631HCID 178516631, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To an anhydrous DMF (5 mL) solution of 5-(3-cyanophenyl)-8,9,10,11-tetrahydronaphtho[2,1-b][1,4]diazepine-2,4(3H,5H)-dione (302 mg, 0.91 mmol) was added tri-n-butyltin azide (499 μL, 1.82 mmol). The mixture was stirred at 110° C. for 24 hours. The reaction mixture was cooled on standing, poured into saturated aqueous sodium hydrogen carbonate solution, and washed with ethyl acetate. After neutralization of the aqueous layer by addition of 1M hydrochloric acid, the layer was extracted with ethyl acetate, washed with purified water, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by chromatography (chloroform/methanol=95/5) to give the titled compound as slightly yellow powder (242 mg, yield 71%).

Workup

  1. temperatureThe reaction mixture was cooled on standing
  2. washwashed with ethyl acetate
  3. additionAfter neutralization of the aqueous layer by addition of 1M hydrochloric acid
  4. extractionthe layer was extracted with ethyl acetate
  5. washwashed with purified water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customThe residue was purified by chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-f6641430b67e4468bae43277c4469083
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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