1,3-Dibromo-5,5-dimethylhydantoin → HCID 59232103, compound

HRID 1099307Notes

Reaction equation

HRID 1099307 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([CH:13]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:26]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([Br:26])[CH:9]=[C:10]([C:11]([CH:13]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59232095HCID 59232095, compound

Product 1

HCID 59232103HCID 59232103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)carbonyl]morpholine-4-carboxylate (0.66 g, 1.90 mmol) in THF (5 mL) was cooled to −50° C. and stirred for 1 h before adding 1.3-dibromo-5,5-dimethylhydantoin (0.27 g, 0.94 mmol) in portions. The reaction was then quenched with satd. Na2SO3 solution. The product was extracted with EtOAc, dried (MgSO4) and concentrated. The crude solid was triturated with EtOAc and filtered. An off-white solid was isolated (530 mg, 65%). 1H-NMR (DMSO-d6) δ 8.10 (s, 1 H), 7.54 (s, 1 H), 5.05-4.95 (m, 1 H), 4.00-3.89 (m, 2H), 3.69-3.55 (m, 2 H), 3.10-3.00 (m, 2 H), 1.33 (bs, 9 H).

Workup

  1. customThe reaction was then quenched with satd
  2. extractionThe product was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude solid was triturated with EtOAc
  6. filtrationfiltered
  7. customAn off-white solid was isolated (530 mg, 65%)

Sources & evidence

ORD record
ord-39c13cb9029143788a4f4d199c576dd4
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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