1,2-Dichloroethane → HCID 21084086, compound

HRID 347919Notes

Reaction equation

HRID 347919 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]2[S:14][C:15]([C:23](O)=[O:24])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5]=2[CH:4]=[CH:3]1.[CH2:26]([NH2:29])[CH:27]=[CH2:28].C(N(CC)CC)C.C(Cl)CCl.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:26]([NH:29][C:23]([C:15]1[S:14][C:6]2[N:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2](=[O:1])[CH:3]=[CH:4][C:5]=2[C:16]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:24])[CH:27]=[CH2:28]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 7853AllylamineHCID 8471TriethylamineHCID 21083991HCID 21083991, compound

Product 1

HCID 21084086HCID 21084086, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound of Example 59 (174 mg, 0.5 mmol) in dry DCM (5 mL) was added allyl amine (29 mg, 0.5 mmol), triethylamine (101 mg, 1 mmol), and a catalytic amount of 4-dimethylaminopyridine followed by EDC (96 mg, 0.5 mmol). The reaction mixture was stirred at r.t. for 4 h and then poured into 2M HCl(aq) (20 mL). The product was extracted with DCM (2×20 mL) and the combined organic fractions dried (MgSO4), filtered and the solvent removed in vacuo. Purification by radial chromatography (silica, EtOAc) gave the title compound as a solid (70 mg). δH (CDCl3) 7.7–7.1 (11H, m), 4.48 (1H, d, J 10 Hz), 5.6–5.4 (1H, m), 5.28 (1H, bs), 4.84 (1H, dd, J 10, 1 Hz), 4.69 (1H, dd, J 10, 1 Hz), 3.8–3.6 (2H, m). LCMS (ES+) 387 (M+H)+.

Workup

  1. extractionThe product was extracted with DCM (2×20 mL)
  2. dry with materialthe combined organic fractions dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customPurification by radial chromatography (silica, EtOAc)

Sources & evidence

ORD record
ord-1319cd8dfbe24059a18ba02637bd89f7
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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