1,2-Dichloroethane → HCID 58790107, compound

HRID 2193754Notes

Reaction equation

HRID 2193754 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([N:16]4[CH2:20][CH2:19][CH2:18][C:17]4=[O:21])[S:15][C:8]=23)=[C:4]([F:24])[CH:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][C:34](=[O:39])[CH2:35][C:36](O)=[O:37].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.CC#N>[F:24][C:4]1[CH:3]=[C:2]([NH:1][C:36](=[O:37])[CH2:35][C:34]([NH:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])=[O:39])[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[S:15][C:8]=12

Participants

8

Reactant 4

HCID 111,2-Dichloroethane2×HCID 757711-HydroxybenzotriazoleHCID 12664594N-(2-Methoxy-phenyl)-malonamic acid2×HCID 58790249HCID 58790249, compound

Product 1

HCID 58790107HCID 58790107, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the amino lactam 285 (80.7 mg, 0.243 mmol), 3-(2-methoxyphenylamino)-3-oxopropanoic acid 27 (76.1 mg, 0.365 mmol), EDC (70 mg, 0.365 mmol) and HOBt (56 mg, 0.365 mmol) in DMF (2.4 mL) was stirred overnight at room temperature. More 27 (76.1 mg, 0.365 mmol) and EDC (70 mg, 0.365 mmol) were added and the mixture was stirred 6 h more. The mixture was diluted with EtOAc, extracted with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was crystallized from MeCN affording title compound 284 (24 mg, 0.044 mmol, 18% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.73 (s, 1H), 9.63 (s, 1H), 8.64 (d, J=6.5 Hz, 1H), 8.06 (dd, J=10 Hz, J=1.5 Hz, 1H), 7.92 (dd. J=13.1 Hz, J=2.3 Hz, 1H), 7.59-7.48 (m, 2H), 7.12-7.05 (m, 3H), 6.94-6.90 (m, 2H), 4.07 (dd, J=7.0 Hz, J=7.4 Hz, 2H), 3.86 (s, 3H), 3.67 (s, 2H), 2.69 (dd, J=7.8 Hz, J=8.2 Hz, 2H), 2.24 (m, 2H). MS (m/z): (M+1) 535.1 (100%).

Workup

  1. extractionextracted with water
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad5f1ba0408f40208d752f15b61e5fd9
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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