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1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-7-(3-methoxyphenyl)-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1615465
Notes
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Reaction equation

HRID 1615465 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:17]3[C:12]([C:13]([NH2:18])=[N:14][CH:15]=[N:16]3)=[CH:11][C:10]=2[CH2:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH:6]=[CH:7][CH:8]=1.[Br:27]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[Br:27][C:11]1[C:10]([CH2:19][CH2:20][CH2:21][N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:17]2[C:12]=1[C:13]([NH2:18])=[N:14][CH:15]=[N:16]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 666020177-(3-Methoxyphenyl)-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 706646535-Bromo-7-(3-methoxyphenyl)-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 161%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (98 mg, 0.28 mmol) prepared in Example 14 in DMF (4 mL) at −40° C. was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (40 mg, 0.14 mmol) portion wise over a period of 1 minute. The reaction was stirred for 30 minutes and was allowed to warm to room temperature, and stirred overnight. DMF was removed, and the crude solid was extracted with sodium hydroxide (1N) and DCM. The organic layer was dried, concentrated to obtain the title compound (97 mg) having the following physical data.

Workup

  1. stirringstirred overnight
  2. customDMF was removed
  3. extractionthe crude solid was extracted with sodium hydroxide (1N) and DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-73899231e7a646d186bf4498ed76c80a
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765754B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes