1,3-Dibromo-5,5-dimethylhydantoin → 5-(2-benzyl-2H-indazol-6-yl)-7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972905Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[CH:19][N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:27]N1C(C)(C)C(=O)N(Br)C1=O.[O-]S([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([Br:27])[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a cooled (−20° C.) solution 5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (600 mg, 1.76 mmol) in THF (18 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (252 mg, 0.88 mmol) in 3 portions over 10 min. The mixture was stirred at −20° C. for 2 h. Saturated, aqueous Na2SO3 (20 mL) was added and the mixture warmed to rt. The mixture was extracted with ethyl acetate (2×20 mL). The combined organics were washed with 5% aqueous K2CO3 (2×20 mL), brine, dried (Na2SO4) and evaporated to provide 660 mg (89%) of the desired product, which contained trace impurities. ES-MS m/z 419.12 [M+H]+, HPLC RT (min) 3.00.

Workup

temperaturethe mixture warmed to rt
extractionThe mixture was extracted with ethyl acetate (2×20 mL)
washThe combined organics were washed with 5% aqueous K2CO3 (2×20 mL), brine
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-4b14a027b2ee4f7ba3ae5fc0c8765e2a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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