1,2-Dichloroethane → HCID 70275469, compound

HRID 322513Notes

Reaction equation

HRID 322513 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[N:4]=1.Cl.[CH2:21]([NH:23][CH2:24][C@H:25]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([I:39])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[C:26]([OH:28])=[O:27])[CH3:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CCOC(C)=O.CN(C=O)C>[CH2:21]([N:23]([C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][C:5]2[N:4]=[C:3]([NH2:2])[CH:8]=[CH:7][CH:6]=2)=[CH:19][CH:18]=1)[CH2:24][C@H:25]([NH:29][S:30]([C:33]1[CH:34]=[CH:35][C:36]([I:39])=[CH:37][CH:38]=1)(=[O:32])=[O:31])[C:26]([OH:28])=[O:27])[CH3:22]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 69370769HCID 69370769, compoundHCID 86754155HCID 86754155, compound

Product 1

HCID 70275469HCID 70275469, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of acid 8-6 (400 mg, 1.43 mmol), amine 8-4 (686 mg, 1.57 mmol), EDC (358 mg, 1.86 mmol), HOBT (252 mg, 1.86 mmol), NMM (632 μl, 5.72 mmol) and DMF (10 ml) was stirred for ˜20 h. The reaction was diluted with EtOAc and then washed with sat NaHCO3, brine, dried (MgSO4) and concentrated. Flash chromatography (silica, EtOAC→5% isopropanol/EtOAc) provided amide 8-7 as a white solid.

Workup

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a3b8b1ed7d404e81a85cc8789454957c
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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