1-Bromo-2-Chloroethane → HCID 89955494, compound

HRID 705347Notes

Reaction equation

HRID 705347 reaction equation
[CH:1]1([C:4]2[C:5]([N:26]([CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[S:27]([CH3:30])(=[O:29])=[O:28])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]4[NH:23][C:22](=[O:24])[O:21][N:20]=4)[C:8]=3[CH:25]=2)[CH2:3][CH2:2]1.Br[CH2:37][CH2:38][Cl:39].N12CCCN=C1CCCCC2>CN(C)C(=O)C>[Cl:39][CH2:38][CH2:37][N:23]1[C:22](=[O:24])[O:21][N:20]=[C:19]1[C:9]1[C:8]2[CH:25]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:5]([N:26]([CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[S:27]([CH3:30])(=[O:28])=[O:29])=[CH:6][C:7]=2[O:11][C:10]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136644184HCID 136644184, compound

Product 1

HCID 89955494HCID 89955494, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 10G (188 mg, 0.376 mmol), 1-bromo-2-chloroethane (0.033 mL, 0.395 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.062 mL, 0.414 mmol) in N,N-dimethylacetamide (6 mL) was heated in a sealed tube at 100° C. for 16 hours, cooled and concentrated. The residue was chromatographed on silica gel eluting with hexane to 3:1 hexane/ethyl acetate to give the title compound as a solid (64 mg, 30%). MS (ESI+) m/z 579 (M+NH4)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was chromatographed on silica gel eluting with hexane to 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-be1d35696e9c4b17ab2783bae7dd667f
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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