O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 11465846, compound

HRID 2250425Notes

Reaction equation

HRID 2250425 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:17]4=[N:18][CH:19]=[CH:20][CH:21]=[C:16]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.Cl.Cl.[CH:49]([N:52]1[CH2:57][CH2:56][CH:55]([NH2:58])[CH2:54][CH2:53]1)([CH3:51])[CH3:50]>CN(C=O)C>[CH:49]([N:52]1[CH2:57][CH2:56][CH:55]([NH:58][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:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[CH:15]=2)=[O:23])[CH2:54][CH2:53]1)([CH3:51])[CH3:50]

Participants

5

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 177503401-(Propan-2-yl)piperidin-4-amine dihydrochlorideHCID 69228934HCID 69228934, compound

Product 1

HCID 11465846HCID 11465846, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.135 g (0.4 mmol) of 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, 0.432 g (3.8 mmol) of NEM and 135 mg (0.4 mmol) of TOTU were dissolved in 3 mL of DMF and stirred at RT for 20 min. 89 mg (0.4 mmol) of 1-Isopropyl-piperidin-4-ylamine dihydrochloride salt was added to the reaction solution and stirred at RT for 4 h. The product was purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). After lyophilization the product was obtained as a solid.

Workup

  1. stirringstirred at RT for 4 h
  2. customThe product was purified by preparative RP-HPLC
  3. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)
  4. customAfter lyophilization the product was obtained as a solid

Sources & evidence

ORD record
ord-788bafa443914febadc50f99c949711a
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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