1,3-Dibromo-5,5-dimethylhydantoin → HCID 59231971, compound

HRID 1972762Notes

Reaction equation

HRID 1972762 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[Br:24]N1C(C)(C)C(=O)N(Br)C1=O>O1CCCC1>[NH2:1][C:2]1[C:7]2=[C:8]([Br:24])[CH:9]=[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 59232077HCID 59232077, compound

Product 1

HCID 59231971HCID 59231971, compoundYield 119.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a cooled (−20° C.) solution of tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate (660 mg, 2.08 mmol) in tetrahydrofuran (10 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (297 mg, 1.04 mmol) in 3 portions over 10 min. The mixture was allowed to stir (−20° C.) for 1 h. The reaction was quenched with the addition saturated aqueous Na2SO3 (10 mL) and was allowed to warm to rt. The mixture was extracted with ethyl acetate (3×20 mL). The combined organics were washed with brine (25 mL), dried (Na2SO4) and evaporated. The crude material was purified by ISCO® chromatography using a gradient of 75 to 100% ethyl acetate in hexanes to afford 494 mg (60%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.83 (s, 1 H), 6.64 (s, 1 H), 4.10-3.96 (m, 2H), 3.29-3.19 (m, 1 H), 1.90 (d, 2 H), 1.55-1.42 (m, 2 H), 1.41 (s, 9 H); ES-MS m/z 396.1 [M+H]+, HPLC RT (min) 2.79.

Workup

  1. customThe reaction was quenched with the addition saturated aqueous Na2SO3 (10 mL)
  2. temperatureto warm to rt
  3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  4. washThe combined organics were washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude material was purified by ISCO® chromatography

Sources & evidence

ORD record
ord-ede10f1f466b4347853bc79c768aba7a
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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