Triethylamine → 5'-(6-(Indoline-1-carbonyl)pyrimidin-4-ylamino)-3-methyl-1',3'-dihydrospiro[imidazolidin-4,2'-inden]-2,5-dione

HRID 1640267Notes

Reaction equation

HRID 1640267 reaction equation
[CH3:1][N:2]1[C:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]4[N:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=O)[CH:17]=4)[CH:12]=3)[CH2:7]2)[C:5](=[O:25])[NH:4][C:3]1=[O:26].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[N:27]1([C:22]([C:18]2[N:19]=[CH:20][N:21]=[C:16]([NH:15][C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[CH2:7][C:6]3([C:5](=[O:25])[NH:4][C:3](=[O:26])[N:2]3[CH3:1])[CH2:14]4)[CH:17]=2)=[O:24])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10328IndolineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 581175346-(3-Methyl-2,5-dioxo-1',3'-dihydrospiro[imidazolidin-4,2'-inden]-5'-ylamino)pyrimidine-4-carboxylic acid

Product 1

HCID 426102585'-(6-(Indoline-1-carbonyl)pyrimidin-4-ylamino)-3-methyl-1',3'-dihydrospiro[imidazolidin-4,2'-inden]-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.0 mg (0.23 mmol) 6-(3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidin-4,2′-inden]-5′-ylamino)pyrimidine-4-carboxylic acid, 30 μL (0.27 mmol) 2,3-dihydro-1H-indole, 70 μL (0.50 mmol) triethylamine and 80.0 mg (0.25 mmol) TBTU in 1.5 mL DMF were stirred for 4 h at RT. The reaction mixture was filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined, concentrated by rotary evaporation and dried.

Workup

  1. filtrationThe reaction mixture was filtered through a syringe
  2. filtrationfilter
  3. custompurified by preparative HPLC
  4. concentrationconcentrated by rotary evaporation
  5. customdried

Sources & evidence

ORD record
ord-aa35150c83c345f69980fd03117f6838
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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