Triethylamine → HCID 86594575, compound

HRID 1744134Notes

Reaction equation

HRID 1744134 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[C:10]([NH:32][C@H:33]([C:38]([OH:40])=O)[CH2:34][CH:35]([CH3:37])[CH3:36])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](O[N:58]2N=[N:65][C:60]3C=CC=C[C:59]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:59]([CH2:60][NH:65][C:38](=[O:40])[C@H:33]([CH2:34][CH:35]([CH3:36])[CH3:37])[NH:32][C:10]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]=1)#[N:58]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 69152735HCID 69152735, compound

Product 1

HCID 86594575HCID 86594575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucine (864 mg, 1.55 mmol), PyBOP (890 mg, 1.71 mmol), aminoacetonitrile hydrochloride (315 mg, 3.41 mmol) in dry DMF (40 mL) under dry nitrogen was added triethylamine (0.76 mL, 5.43 mmol) dropwise and the reaction was stirred for 4½ hours. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6) to afford N1-(cyanomethyl)-N2-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucinamide.

Workup

  1. extractionthe product extracted with Et2O (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6)

Sources & evidence

ORD record
ord-4b2fe9ccf99c48c4b070e5dc1e1e8117
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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