1,2-Dichloroethane → HCID 58001342, compound

HRID 1945450Notes

Reaction equation

HRID 1945450 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([OH:14])=O)=[O:7].C(Cl)CCl.C1C=CC2N(O)N=[N:33][C:31]=2C=1.[CH3:37][CH2:38][N:39]([CH:43]([CH3:45])C)[CH:40]([CH3:42])C.CN(C=[O:50])C>>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][N:17]=1)[C:12]([NH:33][CH2:31][CH2:45][CH2:43][N:39]1[CH2:38][CH2:37][O:50][CH2:42][CH2:40]1)=[O:14])=[O:7]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 580013332-[2-(2,4-Dichloro-phenoxy)acetylamino]-isonicotinic acid

Product 1

HCID 58001342HCID 58001342, compoundYield 21.7%

Procedure

To solution of 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid (100 mg, 0.31 mmol), 3-morpholine-4-propylamine (67.8 mg, 0.07 ml, 0.47 mmol), EDC (90.1 mg, 0.47 mmol) and HOBt (63.4 mg, 0.47 mmol) in DMF 4 ml was added DIPEA (60.7 mg, 0.08 ml, 0.47 mmol), and stirred. Reaction mixture was then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by preparative-TLC(CH2Cl2:MeOH=6:1) to afford 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-N-(3-morpholine-4-yl-propyl)isonicotinamide as a white solid (31.3 mg, 21.7% yield).

Workup

  1. customReaction mixture
  2. customwas then partitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative-TLC(CH2Cl2:MeOH=6:1)

Sources & evidence

ORD record
ord-78be5917f22647749d611fc33e9d1395
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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