1,2-Dichloroethane → HCID 11596497, compound

HRID 416306Notes

Reaction equation

HRID 416306 reaction equation
[C:1]([NH:9][C@H:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:24]1([NH2:31])[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH2:30].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(#N)C>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:31][C:19]([C:18]1[CH:17]=[CH:16][C:15]([N:12]2[CH2:13][CH2:14][C@H:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=3)[CH2:11]2)=[CH:23][CH:22]=1)=[O:21]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 58930567HCID 58930567, compound

Product 1

HCID 11596497HCID 11596497, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 399 (93 mg, 0.3 mmol), phenylene diamine (65 mg, 0.6 mmol), EDC (86 mg, 0.45 mmol), HOBT (53 mg, 0.33 mmol) and Et3N (125 μL, 91 mg, 0.9 mmol) in acetonitrile (2 mL) was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was purified by flash chromatography using the gradient 5-20% MeOH in DCM as an eluent to afford the title compound (24 mg, 16% yield). 1H NMR (CDCl3) δ 8.97 (s, 1H), 8.66 (d, J=4.9 Hz, 1H), 8.21 (d, J=3.9 Hz, 1H), 7.87 (d, 2H, J=8.8 Hz), 7.52 (dd, J=5.1 Hz, J=8.0 Hz, 1H), 7.15 (d, 1H, J=7.9 Hz), 7.05 (t, J=8.1 Hz, 1H), 6.89 (d, J=7.6 Hz, 1H), 6.76 (t, J=7.3 Hz, 1H), 6.66 (d, J=9.0 Hz, 2H), 4.78 (m, 1H), 3.80 (dd, J=6.7 Hz, J=10.2 Hz, 1H), 3.61 (m, 1H), 3.49 (m, 1H), 3.41 (m, 1H), 2.4 (m, 1H), 2.2 (m, 1H). LRMS: (calc) 401.2; (found) 402.2 (M+H1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1790f7110cea457eb22f37851747052f
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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