1,2-Dichloroethane → HCID 21084087, compound

HRID 347908Notes

Reaction equation

HRID 347908 reaction equation
C(Cl)CCl.C1C=C[C:8]2N(O)N=[N:11][C:9]=2C=1.[O:15]=[C:16]1[N:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:20]2[S:28][C:29]([C:37](O)=[O:38])=[C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:19]=2[CH:18]=[CH:17]1.Cl.C(N)C.CN1CCOCC1>C(Cl)Cl.O>[CH2:9]([NH:11][C:37]([C:29]1[S:28][C:20]2[N:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16](=[O:15])[CH:17]=[CH:18][C:19]=2[C:30]=1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:38])[CH3:8]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 21083991HCID 21083991, compound

Product 1

HCID 21084087HCID 21084087, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

EDC (66 mg, 0.35 mmol) and HOBT (43 mg, 0.32 mmol) were added to the compound of Example 59 (100 mg, 0.29 mmol) in DCM (2 mL). After 15 min ethylamine hydrochloride (26 mg, 0.32 mmol) and NMM (0.070 mL, 0.63 mmol) were added and the reaction mixture was stirred at r.t. overnight. Water (2 mL) and DCM (2 mL) were added, the suspension filtered through a hydrophobic frit and the organic phase concentrated in vacuo. The crude product was purified by column chromatography on silica (1% MeOH in DCM) to give the title compound as a white solid (95 mg, 88%). δH (DMSO-d6) 7.69–7.61 (3H, m), 7.59–7.49 (3H, m), 7.45 (1H, d, J 9.6 Hz), 7.44–7.42 (4H, m), 7.05 (1H, t, J 5.4 Hz), 6.54 (1H, d, J 9.6 Hz), 3.03 (2H, q, J 7.1 Hz), 0.84 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.33 minutes, 375.0 (M+H)+.

Workup

  1. filtrationthe suspension filtered through a hydrophobic frit
  2. concentrationthe organic phase concentrated in vacuo
  3. customThe crude product was purified by column chromatography on silica (1% MeOH in DCM)

Sources & evidence

ORD record
ord-adf760149ead4ee9b655a02fb629fd1d
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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