O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 68855620, compound

HRID 1071679Notes

Reaction equation

HRID 1071679 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[C:14]3[C:22](O)=[O:23])[CH:8]=2)=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][N:57]([NH2:60])[CH2:56][CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48]>C(Cl)Cl>[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][N:57]([NH:60][C:22]([C:14]2[N:13]([CH2:12][C:9]3[CH:8]=[C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:11][N:10]=3)[C:21]3[C:16]([CH:15]=2)=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:23])[CH2:56][CH2:55]1)=[O:53])([CH3:50])([CH3:48])[CH3:49]

Participants

5

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11222093HCID 11222093, compoundHCID 22029174tert-Butyl 4-aminopiperazine-1-carboxylate

Product 1

HCID 68855620HCID 68855620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-indole-2-carboxylic acid and 1.3 ml NEM in 8 ml DCM, 914 mg TOTU were added and the mixture was stirred for 30 min at RT. Then 673 mg 4-Amino-piperazine-1-carboxylic acid tert-butyl ester were added and the reaction was stirred over night. After removal of the solvent under reduced pressure the residue was directly purified by chromatography on silica gel eluting with an ethyl acetate/heptane gradient. Yield: 1.1 g.

Workup

  1. stirringthe reaction was stirred over night
  2. customAfter removal of the solvent under reduced pressure the residue
  3. customwas directly purified by chromatography on silica gel eluting with an ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-bcbddee132e343a4bb5cce235c9b0767
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

Loading…