Triethylamine → HCID 67014890, compound

HRID 1433103Notes

Reaction equation

HRID 1433103 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][NH:6][C:7]1[N:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][O:21][CH3:22])[C:15]2=[O:23])=[CH:9][N:8]=1)[CH3:3].[Cl:24][C:25]1[S:29][C:28]([O:30][CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[Cl:24][C:25]1[S:29][C:28]([O:30][CH2:31][C:32]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:10]3[CH:9]=[N:8][C:7]([NH:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])=[N:12][CH:11]=3)[C:15](=[O:23])[C@@H:16]2[CH2:20][O:21][CH3:22])=[O:33])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 111831442-[(5-Chlorothiophen-2-yl)oxy]acetic acidHCID 68897867HCID 68897867, compound

Product 1

HCID 67014890HCID 67014890, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound can be prepared by placing 1-[(2-{[N,N-dimethylaminoethyl]-amino}-pyrimidin-5-yl)-methyl]-3-(S)-methoxymethyl-piperazine-2-one, (5-chloro-thiophen-2-yloxy)-acetic acid, 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate and triethylamine in DMF and stirring 8-16 h. The mixture is evaporated and is diluted with ethyl acetate. The organic phase is washed with water, 2 N HCl, 1 N NaOH and brine, is dried (MgSO4) and is evaporated. The residue is purified by flash chromatography (silica gel, 4:1 ethyl acetate/hexanes) to provide the title compound.

Workup

  1. customThe mixture is evaporated
  2. additionis diluted with ethyl acetate
  3. washThe organic phase is washed with water, 2 N HCl, 1 N NaOH and brine
  4. dry with materialis dried (MgSO4)
  5. customis evaporated
  6. customThe residue is purified by flash chromatography (silica gel, 4:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4ecb0a3ce87a4ff7ab28ca3f7d907622
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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