Triethylamine → HCID 12150105, compound

HRID 1884609Notes

Reaction equation

HRID 1884609 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.[CH3:64][O:65][C:66](=[O:74])[CH2:67][CH:68]1[O:73][CH2:72][CH2:71][NH:70][CH2:69]1>CN(C=O)C>[CH3:64][O:65][C:66](=[O:74])[CH2:67][CH:68]1[O:73][CH2:72][CH2:71][N:70]([C:24]([C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([NH:13][C:12]([NH:11][C:9]3[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:8]=3[O:28][CH3:29])=[O:27])=[CH:15][CH:16]=2)=[O:25])[CH2:69]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12150104HCID 12150104, compoundHCID 12150106Methyl (morpholin-2-yl)acetate

Product 1

HCID 12150105HCID 12150105, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

95 mg (0.24 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, 139 mg (0.44 mmol) of TBTU, and 102 microL (0.73 mmol) of triethylamine. The clear yellow solution was stirred for 5 min, then 50 mg (0.31 mmol) of morpholin-2-yl-acetic acid methyl ester (Loftus, F. Syn. Commun. 1980, 10, 59) 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 provide an amber oil which was purified on silica gel, eluting with 5% MeOH-methylene chloride to provide 93 mg (72%) of the title compound as a viscous oil.

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. customprovide an amber oil which
  8. customwas purified on silica gel
  9. washeluting with 5% MeOH-methylene chloride

Sources & evidence

ORD record
ord-4b4900b1e96e4fc4ab660786fddda639
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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