Triethylamine → HCID 12150107, compound

HRID 1884610Notes

Reaction equation

HRID 1884610 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:8]([O:28][CH3:29])=[C:9]([NH:11][C:12](=[O:27])[NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24](O)=[O:25])=[CH:16][CH:15]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[OH:64][CH:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]1>CN(C=O)C>[C:1]([C:5]1[CH:10]=[C:9]([NH:11][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24]([N:68]3[CH2:69][CH2:70][CH:65]([OH:64])[CH2:66][CH2:67]3)=[O:25])=[CH:16][CH:15]=2)=[O:27])[C:8]([O:28][CH3:29])=[C:7]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12150104HCID 12150104, compound

Product 1

HCID 12150107HCID 12150107, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

85 mg (0.22 mmol) of 4-[3-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalene-1-carboxylic acid (Example 17) was dissolved in 1 mL of DMF. To this clear solution was added sequentially, 92 mg (0.294 mmol) of TBTU, and 82 microL (0.59 mmol) of triethylamine. The clear yellow solution was stirred for 5 min, then 33 mg (0.33 mmol) of 4-hydroxypiperidine was added. The reaction was stirred overnight, then concentrated in vacuo. The resulting amber oil was extracted with EtOAc and water, brine, and then dried over magnesium sulfate. Concentration in vacuo provided an amber oil which was purified on silica gel, eluting with with 33% EtOAc-hexane to provide 57 mg (54%) of the title compound as a pale white solid.

Workup

  1. additionTo this clear solution was added sequentially
  2. stirringThe reaction was stirred overnight
  3. concentrationconcentrated in vacuo
  4. extractionThe resulting amber oil was extracted with EtOAc and water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo
  7. customprovided an amber oil which
  8. customwas purified on silica gel
  9. washeluting with with 33% EtOAc-hexane

Sources & evidence

ORD record
ord-0d3bf826aacf44f1953fa0236e2423ba
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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