1,2-Dichloroethane → HCID 68772755, compound

HRID 2191087Notes

Reaction equation

HRID 2191087 reaction equation
[CH3:1][C:2]1([CH3:33])[CH2:31][C:6]2[C:7]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28](O)=[O:29])[CH:23]=4)[CH:17]=3)=[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:9][C:5]=2[C:4](=[O:32])[CH2:3]1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:1][C:2]1([CH3:33])[CH2:31][C:6]2[C:7]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([C:28]([N:34]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[O:29])[CH:23]=4)[CH:17]=3)=[C:8]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[S:9][C:5]=2[C:4](=[O:32])[CH2:3]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 68772873HCID 68772873, compound

Product 1

HCID 68772755HCID 68772755, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 223 (55 mg, 0.12 mmol), morpholine (12 mL, 0.14 mmol), EDC (46 mg, 0.24 mmol) and 1-hydroxybenzotriazole hydrate (3 mg, 0.02 mmol) in DCM (10 mL) was stirred at room temperature for 18 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (pH 2.5) to give the title compound (31 mg, 49%) as a yellow oil. δH (CDCl3) 8.82 (1H, dd, J 5.1, 0.6 Hz), 8.73 (1H, dd, J 5.1, 0.4 Hz), 8.30 (1H, d, J 1.1 Hz), 8.04 (1H, dd, J 5.1, 1.7 Hz), 7.91 (1H, s), 7.38 (1H, dd, J 4.9, 1.3 Hz), 3.90-3.81 (4H, m), 3.77-3.71 (4H, m), 3.70-3.65 (4H, m), 3.05-2.98 (4H, m), 2.51 (2H, s), 2.47 (2H, s), 1.05 (6H, s). LCMS (ES+) 533.3 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (pH 2.5)

Sources & evidence

ORD record
ord-864cc0cbfdbc49f6b033d9a4c52e98d6
Source dataset
uspto-grants-2012_12
Patent number
US08324204B2

Reaction notes

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