Diisopropylethylamine → HCID 68948762, compound

HRID 1392203Notes

Reaction equation

HRID 1392203 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]([OH:18])=O)=[CH:11][CH:10]=3)=[CH:3][CH:2]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=[N:30]OC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)C(C)C)C.[NH2:50][C@@H:51]([CH2:56][CH2:57][CH2:58][NH:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[C:52](OC)=[O:53]>CN(C=O)C>[C:60]1([NH:59][CH2:58][CH2:57][CH2:56][CH:51]([NH:50][C:16]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[CH:15]3)=[O:18])[C:52]([NH2:30])=[O:53])[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11379407HCID 11379407, compoundHCID 86588568HCID 86588568, compound

Product 1

HCID 68948762HCID 68948762, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.63 g (2.64 mmol) of 2-pyridin-4-yl-1H-indole-5-carboxylic acid, prepared as in process variant B), was suspended in 150 ml of DMF and admixed successively with 1.01 g (3.08 mmol) of TOTU and 0.63 ml (3.71 mmol) of ethyidiisopropylamine. The mixture was stirred at RT for 20 min, and 0.73 g (3.28 mmol) of methyl (S)-2-amino-3-phenylaminoethylpropionate, prepared according to a), was added to the resulting clear solution. The mixture was stirred under reduced pressure for 15 h and the methyl ester of the title compound was then isolated by flash chromatography over silica gel (DCM:MeOH=19:1). Yield: 0.44 g, empirical formula C26H26N4O3; M.W.=442.2; MS (M+H) 443.3.

Workup

  1. additionwas added to the resulting clear solution
  2. stirringThe mixture was stirred under reduced pressure for 15 h

Sources & evidence

ORD record
ord-f17d1bba5f6743478d083c6dcecc1861
Source dataset
uspto-grants-2008_03
Patent number
US07342029B2

Reaction notes

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