1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529796, compound

HRID 1973005Notes

Reaction equation

HRID 1973005 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][C:22]([CH3:27])=[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:28]N1C(C)(C)C(=O)N(Br)C1=O>ClCCl>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([Br:28])[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][C:22]([CH3:27])=[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

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529692HCID 58529692, compound

Product 1

HCID 58529796HCID 58529796, compoundYield 186.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 5-(2-benzyl-2H-indazol-6-yl)-2-methylpyrrolo[2,1-f][1,2,4]triazin-4-amine (130 mg, 0.367 mmol) in dichloromethane (10 mL) was cooled (−30° C.) under nitrogen atmosphere, and a solution of 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione (52.4 mg, 0.183 mmol) in dichloromethane (10 mL) was added dropwise. After 35 min, the mixture was concentrated in vacuo and purified via MPLC (hexanes/ethyl acetate gradient) to afford 148 mg (93%) of sand-colored solid. 1H-NMR (CD2Cl2): δ 8.04 (d, 1 H), 7.77 (dd, 1 H), 7.73 (dd, 1 H), 7.40-7.31 (m, 5 H), 7.18 (dd, 1 H), 6.75 (s, 1 H), 5.61 (s, 2 H), 5.52 (br s, 2 H), 2.41 (s, 3 H). MS: LC/MS (+esi), m/z=433 [M+H]. RT=2.88 min.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompurified via MPLC (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-7e934323415940f5ad83422b94be3760
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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