1,2-Dichloroethane → HCID 123453589, compound

HRID 1509256Notes

Reaction equation

HRID 1509256 reaction equation
[NH2:1][C:2]1[C:3]([NH:32][CH2:33][CH2:34][C:35]([OH:37])=O)=[N:4][C:5]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[C:28]([O:27][C:25](=[O:26])[NH:24][C:20]1([C:17]2[CH:18]=[CH:19][C:14]([C:5]3[C:6]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)=[CH:7][C:2]4[NH:1][C:35](=[O:37])[CH2:34][CH2:33][NH:32][C:3]=4[N:4]=3)=[CH:15][CH:16]=2)[CH2:21][CH2:22][CH2:23]1)([CH3:30])([CH3:31])[CH3:29]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 67261080HCID 67261080, compound

Product 1

HCID 123453589HCID 123453589, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-((3-amino-6-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-5-phenylpyridin-2-yl)amino)propanoic acid (100 mg, 0.20 mmol) in dry DMF (1 ml) was added EDC (153 mg, 0.80 mmol) and HOBT (122 mg, 0.796 mmol) under nitrogen. The resulting mixture was stirred overnight at room temperature. Water was added and the mixture was extracted with EtOAc (3×10 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 55% EtOAc in cyclohexane) to give the title compound (68 mg, 71%). 1H NMR (500 MHz, CDCl3): 8.38 (1H, br s), 7.94 (1H, br s), 7.72-7.12 (8H, m), 7.01-6.99 (2H, m), 5.00 (1H, s), 3.68-3.66 (2H, m), 2.82-2.80 (2H, m), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br)

Workup

  1. extractionthe mixture was extracted with EtOAc (3×10 ml)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 55% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-96d519b0bc3f4bdbbb3f3a72dd3945d5
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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