1,2-Dichloroethane → HCID 58767495, compound

HRID 639929Notes

Reaction equation

HRID 639929 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([C:21]([OH:23])=O)[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2)#[N:2].[Cl-].[O:25]1[CH2:29][CH2:28][CH:27]([NH3+:30])[CH2:26]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:1]([C:3]1[N:4]=[C:5]([C:21]([NH:30][CH:27]2[CH2:28][CH2:29][O:25][CH2:26]2)=[O:23])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH:10][C:9]([O:19][CH3:20])=[CH:8][CH:7]=2)#[N:2]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 68519727HCID 68519727, compoundHCID 178479574HCID 178479574, compound

Product 1

HCID 58767495HCID 58767495, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF was added to a vial containing 3-cyano-6-methoxy-4-pyridin-2-ylisoquinoline-1-carboxylic acid (0.028 g, 0.092 mmol), tetrahydrofuran-3-aminium chloride ( 0.068 g, 0.550 mmol), EDC (0.105 g, 0.550 mmol) and HOAT (0.0437 g, 0.275 mmol). DIEA (0.071 g, 0.550 mmol) was added to this mixture and stirred at rt overnight. Partitioned between half-saturated bicarb and EtOAc. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated, then purified by reverse phase HPLC to give a tan solid (0.019 g, 55%).

Workup

  1. customPartitioned between half-saturated bicarb and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-75cd0a45d88b40e2bd648c04789c8a3b
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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