1,2-Dichloroethane → HCID 42640262, compound

HRID 2427863Notes

Reaction equation

HRID 2427863 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:33][O:34][C:35]1[C:40]2[O:41][C:42]3[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][C:43]=3[C:39]=2[C:38]([CH:51](OC(=O)C2C=CC=CC=2)[CH2:52][C:53]2[C:58]([Cl:59])=[CH:57][N:56]=[CH:55][C:54]=2[Cl:60])=[CH:37][CH:36]=1>O1CCCC1.CN(C1C=CN=CC=1)C>[Cl:59][C:58]1[CH:57]=[N:56][CH:55]=[C:54]([Cl:60])[C:53]=1[CH2:52][CH:51]([O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([O:15][CH:16]([F:17])[F:18])=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:7]=1)[C:38]1[CH:37]=[CH:36][C:35]([O:34][CH3:33])=[C:40]([O:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)[CH:39]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 23940063-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic AcidHCID 42640110HCID 42640110, compound

Product 1

HCID 42640262HCID 42640262, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-cyclopropylmethoxy-4-difluoromethoxybenzoic acid (268 mg, 1.04 mmoles) is dissolved in dry tetrahydrofuran (30 mL) and EDC (237 mg, 1.24 mmoles), HOBT (190 mg, 1.24 mmoles), TEA (0.172 mL, 1.24 mmoles), DMAP (30 mg) are added to the solution. The mixture is stirred at room temperature for 40 minutes, then Benzoic acid 1-(4-methoxy-8-nitro-dibenzofuran-1-yl)-2-(3,5-dichloro-pyridin-4-yl)-ethyl ester is added and the reaction mixture is stirred at 70° C. for 32 hours. The solvents are then evaporated and the crude mixture is purified by chromatography on SiO2 (hexane:AcOEt from 10:1 to 7:3) to afford 300 mg of the pure title compound.

Workup

  1. stirringthe reaction mixture is stirred at 70° C. for 32 hours
  2. customThe solvents are then evaporated
  3. customthe crude mixture is purified by chromatography on SiO2 (hexane:AcOEt from 10:1 to 7:3)

Sources & evidence

ORD record
ord-53c7184b5e6c4fc98d6ac9898f4ed80e
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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