1,2-Dichloroethane → 3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

HRID 1678773Notes

Reaction equation

HRID 1678773 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[NH:30][C:29]([C:31]5[N:36]=[CH:35][CH:34]=[CH:33][N:32]=5)=[N:28][N:27]=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].C1C=CC2N(O)N=NC=2C=1.[CH3:53][N:54]1[CH:58]=[C:57]([C:59](O)=O)[N:56]=[CH:55]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.C(O)(=O)C>[CH3:53][N:54]1[CH:58]=[C:57]([C:59]2[N:12]3[C:3]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[C:7]([C:13]5[CH:18]=[CH:17][C:16]([CH2:19][N:20]6[CH2:21][CH2:22][CH:23]([C:26]7[NH:30][C:29]([C:31]8[N:36]=[CH:35][CH:34]=[CH:33][N:32]=8)=[N:28][N:27]=7)[CH2:24][CH2:25]6)=[CH:15][CH:14]=5)=[N:8][C:9]=4[CH:10]=[CH:11]3)=[N:1][N:2]=2)[N:56]=[CH:55]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5415091-methyl-1H-imidazole-4-carboxylic acidHCID 178514342HCID 178514342, compound

Product 1

HCID 1784812663-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 11-3 (0.23 g, 0.4 mMol), HOBT (0.06 g, 0.45 mMol), and 1-methyl-1H-imidazole-4-carboxylic acid (0.06 g, 0.45 mMol) in anhydrous DMF (2 mL) was added DIEA (0.13 mL, 0.8 mMol) followed by EDC (0.09 g, 0.5 mMol). The solution was heated in the microwave reactor for 15 minutes at 80° C. Solution was then treated with 0.2 mL of acetic acid and was heated to 80° C. in the microwave reactor for 20 minutes. Upon cooling to room temperature, the solution was passed through a syringe filter and purified on a C18 reverse phase HPLC to give 12-1 as a solid. Mass (M+1) calculated: 632.2742 observed: 632.274

Workup

  1. temperaturewas heated to 80° C. in the microwave reactor for 20 minutes
  2. temperatureUpon cooling to room temperature
  3. customthe solution was passed through a syringe
  4. filtrationfilter
  5. custompurified on a C18 reverse phase HPLC

Sources & evidence

ORD record
ord-bf05e73271d44b21928093b65535d432
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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