1,2-Dichloroethane → N-{3-[4-(4-Cyano-3-fluoro-phenyl)-3-methyl-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-3-oxo-propyl}-3-methoxy-benzenesulfonamide

HRID 1700175Notes

Reaction equation

HRID 1700175 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]2[C:15]3[N:16]([CH3:19])[CH:17]=[N:18][C:14]=3[CH2:13][CH2:12][NH:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([S:28]([NH:31][CH2:32][CH2:33][C:34](O)=[O:35])(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([CH:10]2[C:15]3[N:16]([CH3:19])[CH:17]=[N:18][C:14]=3[CH2:13][CH2:12][N:11]2[C:34](=[O:35])[CH2:33][CH2:32][NH:31][S:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=2)(=[O:30])=[O:29])=[CH:9][C:2]=1[F:1])#[N:5]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 183178222-Fluoro-4-(3-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-4-yl)-benzonitrileHCID 186294403-(3-Methoxy-benzenesulfonylamino)-propionic acid

Product 1

HCID 18317823N-{3-[4-(4-Cyano-3-fluoro-phenyl)-3-methyl-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-3-oxo-propyl}-3-methoxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Fluoro-4-(3-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-4-yl)-benzonitrile (Step E) (0.034 g, 0.132 mmol), 3-(3-methoxy-benzenesulfonylamino)-propionic acid (Step G) 0.041 g, 0.16 mmol), HOBT (0.022 g, 0.16 mmol), EDC (0.031 g, 0.16 mmol) and N-methylmorpholine (0.043 mL, 0.40 mmol) were dissolved in DMF (3 mL) and stirred for 18 h. The reaction mixture was concentrated in vacuo, diluted with CH2Cl2 and saturated NaHCO3 solution and separated. The aqueous layer was washed with CH2Cl2 (2×, the organic layers combined, dried (Na2SO4), filtered and concentrated to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with CH2Cl2 and saturated NaHCO3 solution
  3. customseparated
  4. washThe aqueous layer was washed with CH2Cl2 (2×
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2c03fc6a8231416890f8bd448c8f16f9
Source dataset
uspto-grants-2002_02
Patent number
US06350755B1

Reaction notes

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