1,2-Dichloroethane → HCID 21084088, compound

HRID 347910Notes

Reaction equation

HRID 347910 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[O:6]=[C:7]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:11]2[S:19][C:20]([C:28](O)=[O:29])=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]=2[CH:9]=[CH:8]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[CH3:5][O:4][N:3]([CH3:2])[C:28]([C:20]1[S:19][C:11]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:6])[CH:8]=[CH:9][C:10]=2[C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:29]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21083991HCID 21083991, compound

Product 1

HCID 21084088HCID 21084088, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,O-Dimethylhydroxylamine hydrochloride (31 mg, 0.32 mmol) was added to a mixture of the compound of Example 59 (101 mg, 0.29 mmol), HOBT (55 mg, 0.41 mmol), EDC (78 mg, 0.41 mmol) and NMM (0.090 mL, 0.81 mmol) in DCM (3 mL). The mixture was stirred for 6 h at room temperature. DCM was added and the mixture washed with 2M HCl(aq). The organic phase was re-extracted with DCM. The combined organics were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica (3.5% MeOH in DCM) to give the title compound as a white solid (95 mg, 84%). δH (DMSO-d6) 7.48–7.35 (3H, m), 7.34–7.30 (3H, m), 7.29–7.23 (3H, m), 7.16–7.13 (2H, m), 6.33 (1H, d, J 9.6 Hz), 3.26 (3H, s), 2.79 (3H, s). LCMS (ES+) RT 3.27 minutes, 391.0 (M+H)+.

Workup

  1. washthe mixture washed with 2M HCl(aq)
  2. extractionThe organic phase was re-extracted with DCM
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica (3.5% MeOH in DCM)

Sources & evidence

ORD record
ord-9490d4b151364edfbf3a8e4dc2336312
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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