Triethylamine → HCID 86596120, compound

HRID 1243140Notes

Reaction equation

HRID 1243140 reaction equation
[CH2:1]([N:3]([CH2:24][CH3:25])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([NH2:23])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)[CH3:2].C([NH:33][CH2:34][C:35](O)=[O:36])(OC(C)(C)C)=O.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:24]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2([NH:23][C:35](=[O:36])[CH2:34][NH2:33])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:8][CH:9]=1)[CH3:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 865961192-Amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide

Product 1

HCID 86596120HCID 86596120, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide (100 mg, 0.3 mmol) from Example 8 and N-Boc-glycine (52 mg, 0.3 mmol) in DMF (1.0 mL) was added Et3N (61 mg, 0.6 mmol) and TBTU (96 mg, 0.3 mmol). The mixture was stirred overnight and the precipitates were collected by filtration(130 mg) and dissolved in dichloromethane (10 mL) and TFA (5.0 mL). The mixture was concentrated under reduced pressure and ethyl acetate (20 mL) were added and the resulting solution was washed with 1N NaOH. The organic phase was dried over MgSO4 and then concentrated under reduced pressure to give 2-(2-amino-acetylamino)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide (70 mg).

Workup

  1. filtrationthe precipitates were collected by filtration(130 mg)
  2. dissolutiondissolved in dichloromethane (10 mL)
  3. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate (20 mL)
  4. additionwere added
  5. washthe resulting solution was washed with 1N NaOH
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed5903f68e394813b29f5c23ff4769ce
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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