1,3-Dibromo-5,5-dimethylhydantoin → HCID 59231934, compound

HRID 1099268Notes

Reaction equation

HRID 1099268 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:23]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:23])[CH:9]=[C:10]([CH:11]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59232074HCID 59232074, compound

Product 1

HCID 59231934HCID 59231934, compoundYield 188.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 3-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)pyrrolidine-1-carboxylate (1.2 g, 3.96 mmol) in DMF (20 mL) was cooled to 40° C. and treated with 1,3-dibromo-5,5-dimethylhydantoin (508 mg, 1.78 mmol). The reaction was allowed to warm slowly to rt over a 2 h period and was then partitioned between EtOAc and bicarbonate solution. After concentration, the residue was triturated with EtOAc to yield the desired product (1.28 g, 85%). 1H-NMR (DMSO): δ 7.86 (s, 1H), 6.69 (s, 1H), 3.68 to 3.80 (m, 2H), 3.36 to 3.46 (m, 1H), 3.20 to 3.30 (m, 2H), 2.16 to 2.30 (m, 1H), 1.98 to 2.08 (m, 1H), 1.37 (s, 9H); MS: LC/MS (+esi), m/z=382.1 [M+H]; LC/MS rt=3.08 min.

Workup

  1. customwas then partitioned between EtOAc and bicarbonate solution
  2. concentrationAfter concentration
  3. customthe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-d6895d71fc654f03b135b414441a3e45
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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