1,2-Dichloroethane → HCID 10128151, compound

HRID 899845Notes

Reaction equation

HRID 899845 reaction equation
[C:1]1([C:11](O)=[O:12])[C:10]2C(=CC=CC=2)C=[CH:3][N:2]=1.C(N(CC)C(C)C)(C)C.[CH:23]1[CH:24]=[CH:25][C:26]2N(O)N=N[C:27]=2[CH:28]=1.C(Cl)CCl.[NH:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[C:38]1[CH2:46][N:47]([CH:52]1[C:61]2[N:60]=[CH:59][CH:58]=[CH:57][C:56]=2[CH2:55][CH2:54][CH2:53]1)[CH2:48][CH2:49][CH2:50][NH2:51]>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.O>[NH:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[N:39]=[C:38]1[CH2:46][N:47]([CH:52]1[C:61]2[N:60]=[CH:59][CH:58]=[CH:57][C:56]=2[CH2:55][CH2:54][CH2:53]1)[CH2:48][CH2:49][CH2:50][NH:51][C:11]([C:1]1[N:2]=[CH:3][C:27]2[C:26]([CH:10]=1)=[CH:25][CH:24]=[CH:23][CH:28]=2)=[O:12]

Participants

10

Reactant 5

HCID 111,2-DichloroethaneHCID 68092Isoquinoline-1-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10308735HCID 10308735, compound

Product 1

HCID 10128151HCID 10128151, compoundYield 54%

Reagents, catalysts & solvents 4

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

Procedure

To a stirred solution of 1-isoquinolinecarboxylic acid (51.6 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 crude material by radial chromatography on a I mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1) gave the free base of the title compound (79.2 mg, 54%) 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 crude material by radial chromatography on a I mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1)

Sources & evidence

ORD record
ord-5b5249df4c56466e8e7ff84f606f02bf
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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