1,2-Dichloroethane → HCID 25064115, compound

HRID 1919603Notes

Reaction equation

HRID 1919603 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([C:10]3[S:11][C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.O.O[N:23]1[C:27]2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C(Cl)CCl.CN>C(Cl)Cl>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([C:10]3[S:11][C:12]([C:16]([NH:23][CH3:27])=[O:18])=[C:13]([CH3:15])[N:14]=3)[CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 25064114HCID 25064114, compound

Product 1

HCID 25064115HCID 25064115, compoundYield 543.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of Example 28 (0.35 g, 0.99 mmol) in DCM (10 mL) were added 1-hydroxybenzotriazole hydrate (0.015 g, 0.11 mmol), DIPEA (0.175 mL, 1.00 mmol) and EDC (210 mg, 1.08 mmol). The reaction mixture was stirred at r.t. for 5 minutes. Methylamine (0.185 mL, 33% wt. solution in EtOH, 1.97 mmol) was added and stirring was continued at r.t. for 20 h. The reaction mixture was then diluted with DCM (100 mL) and then washed with sat. aqueous NaHCO3 solution (100 mL), then water (100 mL) and brine (100 mL). The organic fraction was dried (NaSO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0-10% MeOH/DCM) gave the title compound (0.22 g, 61%) as a white solid. δH (DMSO-d6) 8.07 (1H, d, J 8.5 Hz), 7.83-7.75 (1H, m), 7.19-7.12 (2H, m), 4.34-4.27 (2H, m), 4.04-3.97 (2H, m), 2.70 (3H, d, J 4.5 Hz), 2.47 (3H, s). LCMS (ES+) 368.1 and 370.1 (M+H)+, RT 3.50 minutes (Method 7).

Workup

  1. stirringstirring
  2. waitwas continued at r.t. for 20 h
  3. washwashed with sat. aqueous NaHCO3 solution (100 mL)
  4. dry with materialThe organic fraction was dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-47d1f99f87cc4cdda0ff35718149eaeb
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

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