1,2-Dichloroethane → HCID 10174475, compound

HRID 916973Notes

Reaction equation

HRID 916973 reaction equation
[C:1]([C:3]1[C:4]([O:24][CH2:25][C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=2)=[N:5][C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].Cl.CN.C(Cl)CCl.[CH3:42][N:43]1CCOCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([C:3]1[C:4]([O:24][CH2:25][C:26]2[CH:34]=[CH:33][C:29]([C:30]([NH:43][CH3:42])=[O:32])=[CH:28][CH:27]=2)=[N:5][C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)[CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 6364545Methylamine hydrochlorideHCID 10311138HCID 10311138, compound

Product 1

HCID 10174475HCID 10174475, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dried round bottom flask was added the product of Example 122 (0.030 g; 0.0613 mmol), methylamine hydrochloride (0.005 g; 0.0675 mmol), EDC (0.018 g; 0.0919 mmol), DMAP (0.007 g; 0.0613 mmol), N-methylmorpholine (0.028 mL; 0.251 mmol), and methylene chloride (0.5 mL). The reaction mixture was stirred at room temperature overnight. The volatiles were removed, and the residue was taken up in ethyl acetate, washed with saturated NaHCO3 (2×), water, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification was done by MPLC (silica gel; 0-50% ethyl acetate:hexane) to afford the desired product: m/e=502 (M+1); Rt=4.2 min on LCMS. HPLC/MS: 502 (M+1); Rt=4.20 min

Workup

  1. customThe volatiles were removed
  2. washwashed with saturated NaHCO3 (2×), water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-bd2dc4da1b894848ab83105a03cc53a5
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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