1,2-Dichloroethane → HCID 59318425, compound

HRID 423355

Reaction equation

HRID 423355 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([C:37]([NH:39]O)=[NH:38])[CH:35]=2)[N:30]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:29]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:38]=[C:37]([C:34]3[CH:35]=[C:36]4[C:31](=[CH:32][CH:33]=3)[N:30]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:29]=[C:28]4[Cl:27])[N:39]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 668363-Bromo-4-methoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 178471837ethyl 3-[3-chloro-5-[(Z)-N'-hydroxycarbamimidoyl]indol-1-yl]propanoate

Product 1

HCID 59318425HCID 59318425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The 3-bromo-4-(methyloxy)benzoic acid (commercial: ICN) (243 mg, 1.05 mmol) stirring in DMF (10 ml) was treated with EDC (219 mg, 0.1.14 mmol) followed by HOBt (156 mg, 0.1.14 mmol). The resultant solution was stirred for 10 minutes. Added ethyl 3-{3-chloro-5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D96) (324 mg, 1.05 mmol) and stirred at RT for 45 minutes. The solution was heated at 80° C. for 4 hours then left standing overnight. The solution was heated at 80° C. for a further 4 hours to give one major product. Evaporated off the DMF, added EtOAc (50 ml) and washed with water (50 ml). The EtOAc was washed with sat. aqueous sodium hydrogen carbonate (50 ml) and water (50 ml) then dried over MgSO4. Evaporated off the solvent and crystallised from ethanol to yield the title compound as 280 mg of cream solid. δH (400 MHz, d6-DMSO) 1.10 (3H, t), 2.90 (2H, t), 3.99-4.05 (5H, m), 4.49 (2H, t), 7.38 (1H, d), 7.74 (1H, s), 7.80 (1H, d), 7.97 (1H, d), 8.21-8.23 (2H, m), 8.36 (1H, d). MS (ES) C22H1981Br35ClN3O4 requires 505; found 506 (MH+).

Workup

  1. waitthen left
  2. temperatureThe solution was heated at 80° C. for a further 4 hours
  3. customto give one major product
  4. customEvaporated off the DMF
  5. additionadded EtOAc (50 ml)
  6. washwashed with water (50 ml)
  7. washThe EtOAc was washed with sat. aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  8. dry with materialthen dried over MgSO4
  9. customEvaporated off the solvent
  10. customcrystallised from ethanol

Sources & evidence

ORD record
ord-cf322d11f21f4b97bf8c87d2e910d806
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Linked notes

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