1,3-Dibromo-5,5-dimethylhydantoin → HCID 58529494, compound

HRID 1972712Notes

Reaction equation

HRID 1972712 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:24]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:24])[CH:9]=[C:10]([CH:11]3[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 58529521HCID 58529521, compound

Product 1

HCID 58529494HCID 58529494, compoundYield 167.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)morpholine-4-carboxylate (840 mg, 2.63 mmol) in DMF (20 mL) was cooled to −40° C. and treated with 1,3-dibromo-5,5-dimethylhydantoin (376 mg, 1.32 mmol). The reaction was warmed to rt over 3 h, and then partitioned between EtOAc and 1N sodium carbonate. The organic layer was separated and washed with water and brine. After drying with sodium sulfate and removal of the solvent in vacuo, trituration with ether provided the desired compound as a brown solid (880 mg, 84%). 1H-NMR (DMSO): δ 7.89 (s, 1H), 4.88 (dd, 1H, J=10, 3 Hz), 3.95 to 4.06 (m, 1H), 3.82 to 3.91 (m, 1H), 3.70 to 3.79 (m, 1H), 3.55 (ddd, 1H, J=11, 11, 3 Hz), 2.92 to 3.28 (m, 2H), 1.37 (s, 9H); MS: LC/MS (+esi): m/z=400.2 [MH]+; LC/MS rt=2.76 min.

Workup

  1. custompartitioned between EtOAc and 1N sodium carbonate
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialAfter drying with sodium sulfate and removal of the solvent in vacuo, trituration with ether

Sources & evidence

ORD record
ord-dd6b55c7b9224082a611389f8c4ddcfd
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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