Toluene → HCID 22324082, compound

HRID 1767636Notes

Reaction equation

HRID 1767636 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][CH:7]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 178507263HCID 178507263, compound

Product 1

HCID 22324082HCID 22324082, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a stirred solution of 7-amino-3-cyclohexyl-1,2-dihydro-1,2,4-benzothiadiazine-1,1-dioxide (0.5 g; 2 mmol) in dry THF (10 ml) at −70° C. was added a solution of 1.5 M DIBALH in toluene (2.7 ml; 4 mmol) under N2. The reaction mixture was stirred for 2 h at −70° C.; 2 h at −40° C. and then warmed to 0° C. The reaction was quenched with H2O and stirred for 30 min. at 0° C. and left over night without stirring at +5° C. The mixture was evaporated to dryness, resuspended in MeOH and filtered. The isolated solid was washed thoroughly with MeOH and filtered. The combined filtrates was adsorped onto silica gel. Column chromatography (EtOAc) gave 200 mg of product.

Workup

  1. temperature2 h at −40° C. and then warmed to 0° C
  2. customThe reaction was quenched with H2O
  3. stirringstirred for 30 min. at 0° C.
  4. waitleft over night
  5. stirringwithout stirring at +5° C
  6. customThe mixture was evaporated to dryness
  7. filtrationfiltered
  8. washThe isolated solid was washed thoroughly with MeOH
  9. filtrationfiltered

Sources & evidence

ORD record
ord-93c943345fdb4a3c9d530d46d38b4873
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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