1,2-Dichloroethane → HCID 57857117, compound

HRID 1643317Notes

Reaction equation

HRID 1643317 reaction equation
[NH:1]([C:8](=[O:30])[CH2:9][N:10]([CH2:20][C:21](=[O:29])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.[CH:35]1[CH:36]=[CH:37][C:38]2[N:43](O)N=[N:41][C:39]=2[CH:40]=1.C1(N)C=CC=CC=1N>CN(C=O)C.CCOC(C)=O>[NH2:41][C:39]1[CH:40]=[CH:35][CH:36]=[CH:37][C:38]=1[NH:43][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([N:10]([CH2:9][C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:30])[CH2:20][C:21](=[O:29])[NH:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 57857116HCID 57857116, compound

Product 1

HCID 57857117HCID 57857117, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[bis(2-anilino-2-oxoethyl)amino]benzoic acid (20 mg, 0.050 mmol) in DMF was added EDC (28 mg, 0.149 mmol), HOBt (20 mg, 0.149 mmol) and phenylenediamine (27 mg, 0.248 mmol) and the reaction was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (25 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired N-(2-aminophenyl)-4-[bis(2-anilino-2-oxoethyl)amino]benzamide: 1H NMR (600 MHz, DMSO-d6) δ 10.90 (s, 2H), 9.31 (s, 1H), 7.83 (d, J=9.0 Hz, 2H), 7.64 (dd, J=8.6, 1.0 Hz, 4H), 7.33 (m, 4H), 7.07 (m, 3H), 6.89 (t, J=7.8 Hz, 1H), 6.70 (d, J=7.8 Hz, 1H), 6.60 (d, 9.1 Hz, 1H), 6.53 (t, J=7.2 Hz, 1H), 4.79 (s, 2H), 4.42 (s, 4H); MS: cal'd 494.2 (MH+), exp 494.2 (MH+).

Workup

  1. customThe crude reaction mixture
  2. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA)
  7. additiondiluted with EtOAc (20 mL)
  8. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe36928e2dd64e129816354afee9a106
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

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