1,2-Dichloroethane → HCID 54227758, compound

HRID 1741471Notes

Reaction equation

HRID 1741471 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([NH:14][C:15](=[O:33])[CH2:16][C:17]1[N:21]([CH2:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[CH:20]=[N:19][CH:18]=1)[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:34]1([CH2:44][NH2:45])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][N:21]1[C:17]([CH2:16][C:15]([NH:14][CH:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:11]([NH:45][CH2:44][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=2)=[O:13])=[O:33])=[CH:18][N:19]=[CH:20]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 67572403HCID 67572403, compound

Product 1

HCID 54227758HCID 54227758, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the acid prepared in step F (125 mg, 0.276 mmol), 1-naphthylmethylamine (39 μl, 0.28 mmol), HOBT (38.1 mg, 0.28 mmol), and triethylamine (40.0 μl, 0.29 mmol) in DMF (3.0 ml) at 0° C., was added EDC (53.0 mg, 0.28 mmol). The reaction was stirred at room temperature for 4 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine and dried (Na2SO4). The solvent was evaporated in vacuo to afford the title compound.

Workup

  1. washthe organic layer washed with sat. aq NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-12f213f5fa9c4db7a6842772aa9f0af0
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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