1,2-Dichloroethane → HCID 9912198, compound

HRID 1584277Notes

Reaction equation

HRID 1584277 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([CH2:11][N:12]2[C:16]([CH2:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:15][N:14]=[CH:13]2)[NH:2]1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](O)=[O:32].ON1C2C=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([N:2]1[C@H:3]([CH2:11][N:12]2[C:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)=[CH:15][N:14]=[CH:13]2)[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 114613-Methoxybenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 54328958HCID 54328958, compound

Product 1

HCID 9912198HCID 9912198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-{3-[(S)-1,2,3,4-tetrahydro-isoquinolin-3-yl-methyl]-3H-imidazol-4-yl-methyl}-benzonitrile (0.16 g, 0.487 mmol), 3-methoxybenzoic acid (0.074 g, 0.487 mmol), 1-hydroxybenzotriazole (0.075 g, 0.487 mmol), EDC (0.093 g, 0.487 mmol) and N-methylmorpholine (0.2 ml, 1.95 mmol) in 5 ml DMF was stirred for 18 hr at 25° C. The solvent was removed in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The ethyl acetate layer was dried with saturated sodium chloride and magnesium sulfate. Evaporation in vacuo of the ethyl acetate layer yielded the crude product. Purification was done on silica gel using methylene chloride:methanol:amonia hydroxide 98:2:0.2 and yielded the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. dry with materialThe ethyl acetate layer was dried with saturated sodium chloride and magnesium sulfate
  4. customEvaporation in vacuo of the ethyl acetate layer
  5. customyielded the crude product
  6. customPurification

Sources & evidence

ORD record
ord-582b6081bc7e4b3e9c7f8a40d5853c9a
Source dataset
uspto-grants-1999_08
Patent number
US05932590

Reaction notes

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