Diisopropylethylamine → HCID 59568597, compound

HRID 216911Notes

Reaction equation

HRID 216911 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[C:20]([NH2:22])=[O:21].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[NH2:22][C:20](=[O:21])[C@@H:19]([NH:18][C:15]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:17])[CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59568596HCID 59568596, compound

Product 1

HCID 59568597HCID 59568597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxylic acid (374 mg), (S)-2-amino-3-(4′-cyanobiphenyl-4-yl)propanamide (Example 3, step (iii), 405 mg) and N-ethyl-N-isopropylpropan-2-amine (0.664 mL) were dissolved in DMF (10 mL) and to the solution was added TBTU (734 mg). The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was evaporated to dryness, dissolved in dichloromethane (20 mL) and was absorbed onto silica. The product was purified by chromatography on silica eluting with 20% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane and then 100% ethyl acetate to afford after evaporation of the relevant fractions the sub-titled compound (700 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in dichloromethane (20 mL)
  3. customwas absorbed onto silica
  4. customThe product was purified by chromatography on silica eluting with 20% ethyl acetate in isohexane
  5. custom50% ethyl acetate in isohexane and then 100% ethyl acetate to afford
  6. customafter evaporation of the relevant fractions the sub-titled compound (700 mg)

Sources & evidence

ORD record
ord-9a565900734f40298ca770bec58354e8
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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