tert-Butyl hydroperoxide → [3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-(6-bromo-1-methyl-1H-indazol-3-yl)-amine

HRID 925444Notes

Reaction equation

HRID 925444 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH:12][C:13]3[CH:14]=[C:15]([C:19]4([CH3:26])[NH:24][C:23](=S)[CH2:22][O:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[NH4+:27].[OH-].C(OO)(C)(C)C>CO>[NH2:27][C:23]1[CH2:22][O:21][CH2:20][C:19]([C:15]2[CH:14]=[C:13]([NH:12][C:6]3[C:5]4[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[CH:18]=[CH:17][CH:16]=2)([CH3:26])[N:24]=1

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14923Ammonium HydroxideHCID 895005195-[3-(6-Bromo-1-methyl-1H-indazol-3-ylamino)-phenyl]-5-methyl-morpholine-3-thione

Product 1

HCID 71549812[3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-(6-bromo-1-methyl-1H-indazol-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-[3-(6-bromo-1-methyl-1H-indazol-3-ylamino)-phenyl]-5-methyl-morpholine-3-thione (21 mg, 0.049 mmol) in MeOH (1.5 ml) were added NH4OH (0.303 ml of a 25% aq. soln., 273 mg, 1.947 mmol) and tBuOOH (0.101 ml of a 70% aq. soln., 94 mg, 0.730 mmol) and the reaction mixture was allowed to stir at rt for 20 h, quenched with sat. aq. NaHCO3 soln. and diluted with EtOAc. The layers were separated and the aq. layer was twice reextracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to leave the crude title compound that was purified by RP-HPLC (Waters SunFire C18 column, 5 μM, 19×150 mm, gradient 10 to 90% ACN+0.1% TFA).

Workup

  1. customquenched with sat. aq. NaHCO3 soln
  2. additionand diluted with EtOAc
  3. customThe layers were separated
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e9a8f34bf4444c7b1fb8efacf2fb8a1
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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