1,2-Dichloroethane → HCID 15979531, compound

HRID 1678783Notes

Reaction equation

HRID 1678783 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:7]([C:13]1[CH:27]=[CH:26][C:16]([CH2:17][NH:18]C(=O)OC(C)(C)C)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[C:44](O)(=O)[C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)C>[C:28]1([C:6]2[C:7]([C:13]3[CH:27]=[CH:26][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=3)=[N:8][C:9]3[CH:10]=[CH:11][N:12]4[C:44]([C:45]5[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=5)=[N:2][N:1]=[C:3]4[C:4]=3[CH:5]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 5922Isonicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59472955HCID 59472955, compound

Product 1

HCID 15979531HCID 15979531, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 16-2 (0.08 g, 0.2 mMol), HOBT (0.03 g, 0.2 mMol), and isonicotinic acid (0.02 g, 0.2 mMol) in anhydrous DMF (1 mL) was added DIEA (0.08 mL, 0.5 mMol) followed by EDC (0.04 g, 0.2 mMol). The solution was heated in a microwave reactor at 80° C. for 12 min. The solution was then treated with 0.5 mL of acetic acid and was heated in a microwave reactor at 80° C. for 30 minutes. Upon cooling to room temperature, the volatiles were evaporated in vacuo and the solution was filtered through a syringe filter and purified on a C18 reverse phase HPLC to give 16-3 as a solid. Mass (M+1) calculated: 429.1822 observed: 429.1811

Workup

  1. temperaturewas heated in a microwave reactor at 80° C. for 30 minutes
  2. temperatureUpon cooling to room temperature
  3. customthe volatiles were evaporated in vacuo
  4. filtrationthe solution was filtered through a syringe
  5. filtrationfilter
  6. custompurified on a C18 reverse phase HPLC

Sources & evidence

ORD record
ord-9ead08364c2147e3b6e2364b02e39a0f
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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