1,2-Dichloroethane → HCID 11224578, compound

HRID 1270988Notes

Reaction equation

HRID 1270988 reaction equation
C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:15]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[NH:23][C@@H:24]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:25](NCCCN(CC)CC)=[O:26])=[CH:17][CH:16]=1.[CH:50]([NH:53][CH2:54][CH2:55][NH2:56])([CH3:52])[CH3:51].CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[C:15]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[NH:23][C@@H:24]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:25]([NH:56][CH2:55][CH2:54][NH:53][CH:50]([CH3:52])[CH3:51])=[O:26])=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 88098N-IsopropylethylenediamineHCID 11328937HCID 11328937, compound

Product 1

HCID 11224578HCID 11224578, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EDC (0.08 g, 0.42 mmol), HOBT (0.056 g, 0.42 mmol) and (S)-2-(3-biphenyl-4-yl-ureido)-3-phenyl-propionic acid (Example 13, step A)(0.1 g, 0.28 mmol) in DMF (3 mL), N′-isopropyl-ethane-1,2-diamine (0.054 g, 0.42 mmol) was added at rt followed by N-methyl morpholine (0.056 g, 0.55 mmol). The solution was stirred for 6 h, diluted with EtOAc (100 mL), washed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL), and dried (Na2SO4). The solvent was removed, and the residue was purified by flash column chromatography using 0–20% MeOH (1% NH4OH)/CH2Cl2 to afford 0.07 g (57%) of the desired product. MS (electrospray): mass calculated for C27H32N4O2, 444.25; m/z found, 445.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.89 (s, 1H), 8.18 (t, J=5 Hz, 1H), 7.61–7.2 (m, 14H), 6.53 (d, J=8 Hz, 1H), 4.46 (m, 1H), 3.16 (m, 2H), 2.9 (dd, J=13.7, 5.8 Hz, 1H), 2.86 (dd, J=13.7, 7.72 Hz, 1H), 2.79 (m, 1H), 2.58 (m, 2H), 0.98 (d, J=6.2 Hz, 6H).

Workup

  1. additionwas added at rt
  2. washwashed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-8ecd04ad640b481097fb5f2610cec08e
Source dataset
uspto-grants-2007_04
Patent number
US07202269B2

Reaction notes

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