Diisopropylethylamine → HCID 70818855, compound

HRID 331517Notes

Reaction equation

HRID 331517 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)[CH:3]=1.F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[N:45]1([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>ClCCl.CN(C)C=O>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9]([N:48]2[CH2:47][CH2:46][N:45]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:50][CH2:49]2)=[O:11])[CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 70819151HCID 70819151, compound

Product 1

HCID 70818855HCID 70818855, compoundYield 57.03%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(4-iodo-2-pyridyl)-2-methyl-propanoic acid (100 mg, 0.3435 mmol) was added to dichloromethane (5 mL) followed by the addition of [benzotriazol-1-yloxy(dimethylamino)methylene]-dimethyl-ammonium tetrafluoroborate (110.3 mg, 0.3435 mmol), diisopropyl ethyl amine (88.79 mg, 119.7 μL, 0.6870 mmol) and tert-butyl piperazine-1-carboxylate (83.18 mg, 0.4466 mmol). Some N,N-dimethylformamide (1 ml) was added to help dissolution. The mixture was stirred at ambient temperature for 1 hour. The mixture was diluted with dichloromethane, washed with water (×2). The extracted organic layer was dried over MgSO4, filtered and concentrated in vacuo to a solid. The residue was purified by column chromatography (ISCO Companion, 80 g column) loaded with dichloromethane and eluted with 100% diethyl ether. Product fractions were combined and concentrated in vacuo to give the sub-title product as an off-white solid (90 mg, 57.03% Yield). LC/MS m/z 460.1 [M+H]+

Workup

  1. dissolutiondissolution
  2. washwashed with water (×2)
  3. dry with materialThe extracted organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid
  6. customThe residue was purified by column chromatography (ISCO Companion, 80 g column)
  7. washeluted with 100% diethyl ether
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a6a0f83ffb542b596358f5c3f48b356
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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