Dichloromethane → HCID 11712372, compound

HRID 1394849Notes

Reaction equation

HRID 1394849 reaction equation
[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13]C(C(O)=O)=[CH:11][C:10]=3[N:9]3CC(=O)N[C:22]4[CH:27]=[CH:26][CH:25]=N[C:23]=4[C:8]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29][N:30]([CH3:35])[S:31]([NH2:34])(=[O:33])=[O:32].Cl.CN(C)[CH2:39][CH2:40][CH2:41]N=C=NCC.C([O:51][CH2:52][CH3:53])(=O)C.Cl[CH2:55]Cl>CN(C)C1C=CN=CC=1.CN(C=O)C.C(O)(=O)C>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:53]([C:52]([NH:34][S:31]([N:30]([CH3:35])[CH3:29])(=[O:33])=[O:32])=[O:51])=[CH:11][C:10]=3[N:9]3[CH2:8][CH:23]=[CH:22][C:27]4[CH:55]=[CH:41][CH:40]=[CH:39][C:26]=4[C:25]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11588871HCID 11588871, compound

Product 1

HCID 11712372HCID 11712372, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 15 (50 mg, 0.14 mmol), N,N-dimethylsulfamide (21 mg, 0.17 mmol), 4-(dimethylamino)pyridine (17 mg, 0.14 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (40 mg, 0.21 mmol) in dichloromethane (1 mL) and DMF (1 mL) was stirred for 18 hours at 22° C. The mixture was poured into ethyl acetate and dilute aqueous acetic acid. The ethyl acetate layer was washed (water, brine), dried (Na2SO4), filtered, and concentrated. The residue was crystallized from ethyl acetate to provide the desired product (17 mg, 26% yield) as pale yellow crystals. ESI-MS m/z 358 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.20-2.30 (m, 10H), 2.81 (m, 1H), 3.05 (s, 3H), 3.47 (m, 2H), 4.11 (m, 1H,) 4.89 (s, 1H), 6.27 (m, 1H), 6.80 (d, J=10.61 Hz, 1H), 7.38 (m, 4H), 7.51 (m, 1H), 7.89 (d, J=8.42 Hz, 1H), 8.02 (s, 1H), 8.75 (s, 1H).

Workup

  1. washThe ethyl acetate layer was washed (water, brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c89d5b60bcfa4ec5b998e4d4a8f6c5e8
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

Loading…