1,2-Dichloroethane → HCID 69652076, compound

HRID 2213543Notes

Reaction equation

HRID 2213543 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[N:13]1[N:17]=[C:16]([C:18](O)=[O:19])[C:15]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:14]1.[NH2:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][CH:39]=1)[C:33]([O:35][CH3:36])=[O:34].ON1C2C=CC=CC=2N=N1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH3:36][O:35][C:33](=[O:34])[C:32]1[CH:37]=[CH:38][CH:39]=[C:30]([NH:29][C:18]([C:16]2[C:15]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:14][N:13]([C:7]3[C:6]([Cl:5])=[CH:11][CH:10]=[CH:9][C:8]=3[Cl:12])[N:17]=2)=[O:19])[CH:31]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 21957570HCID 21957570, compound

Product 1

HCID 69652076HCID 69652076, compoundYield 62.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (869 mg, 4.53 mmol) was added to a stirred solution of the product from step c (1.10 g, 3.02 mmol), methyl 3-aminobenzoate (685 mg, 4.53 mmol), N-hydoxybenzotriazole (612 mg, 4.53 mmol) and 4-DMAP (cat) in DMF (10 ml). The solution was stirred for 72 h and then diluted with ethyl acetate (40 mL). The solution was washed sequentially with water (40 mL) and twice with brine (40 mL). The organic phase was dried (MgSO4) and the filtrate was evaporated at reduced pressure. The residue was purified by flash column chromatography (100% DCM) to yield the title compound (935 mg, 62%). 1H NMR (CDCl3) 8.71 (1H, br s), 8.21-8.20 (1H, t, J=1.8 Hz), 8.05-8.02 (1H, m), 7.86-7.83 (1H, m), 7.54-7.43 (4H, m), 7.31-7.26 (2H, m), 7.11-7.07 (2H, m), 7.00-6.97 (1H, m), 5.65 (2H, s), 3.92 (3H, s).

Workup

  1. washThe solution was washed sequentially with water (40 mL) and twice with brine (40 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe filtrate was evaporated at reduced pressure
  4. customThe residue was purified by flash column chromatography (100% DCM)

Sources & evidence

ORD record
ord-42fef858c4514251a83621a46b85d859
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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