1,2-Dichloroethane → HCID 59694182, compound

HRID 1624341Notes

Reaction equation

HRID 1624341 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N(CC)C(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1[CH2:42][N:43]([CH:48]1[C:57]2[N:56]=[CH:55][CH:54]=[CH:53][C:52]=2[CH2:51][CH2:50][CH2:49]1)[CH2:44][CH2:45][CH2:46][NH2:47]>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.O>[NH:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[C:34]1[CH2:42][N:43]([CH:48]1[C:57]2[N:56]=[CH:55][CH:54]=[CH:53][C:52]=2[CH2:51][CH2:50][CH2:49]1)[CH2:44][CH2:45][CH2:46][NH:47][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10308735HCID 10308735, compound

Product 1

HCID 59694182HCID 59694182, compoundYield 48%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of picolinic acid (36.7 mg, 0.30 mmol) in anhydrous DMF (3 mL) was added N,N-diisopropylethylamine (0.10 mL, 0.6 mmol), HOBT (48.3 mg, 0.36 mmol), EDC (68.6 mg, 0.36 mmol) and N1-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-propane-1,3-diamine (100 mg, 0.30 mmol). The resultant solution was stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc (40 mL), brine (15 mL) and H2O (5 mL) and the two layers mixed vigorously for 15 minutes. The layers were separated and the organic layer washed with brine (5×15 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the beige foam by radial chromatography on a 1 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1) gave the free base of the title compound (63.0 mg, 48%) as a white foam.

Workup

  1. additionthe two layers mixed vigorously for 15 minutes
  2. customThe layers were separated
  3. washthe organic layer washed with brine (5×15 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the beige foam by radial chromatography on a 1 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1)

Sources & evidence

ORD record
ord-edf41bb9b9e74a929a7aa51cc5c8985d
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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