Isonicotinic Acid → HCID 59420873, compound

HRID 499209Notes

Reaction equation

HRID 499209 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:8]=[C:9]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:19][CH:18]=2)=[O:15])[N:10]([CH3:12])[N:11]=1)([CH3:6])([CH3:5])[CH3:4].CCN(C(C)C)C(C)C.N=C=N.C1C=CC2N(O)N=NC=2C=1.[C:52](O)(=[O:59])[C:53]1[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[C:3]([C:7]1[CH:8]=[C:9]([NH:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:52]([C:53]4[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=4)=[O:59])[CH2:26][CH2:25]3)=[CH:19][CH:18]=2)=[O:15])[N:10]([CH3:12])[N:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 6

HCID 5922Isonicotinic AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 68457786HCID 68457786, compound

Product 1

HCID 59420873HCID 59420873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 75 mg (0.17 mmol) of 1-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-(4-piperazin-1-ylmethyl-phenyl)-urea dihydrochloride in methylene chloride (5 mL) is added DIEA (0.103 mL, 0.6 mmol), PS-carbodiimide (266 mg, 0.34 mmol), HOBT (23 mg, 0.17 mmol) and then isonicotinic acid (21 mg, 0.17 mmol). The reaction mixture is shaken at room temperature overnight. Next, PS-trisamine (150 mg) is added and the reaction mixture shaken at room temperature for 2 hr. The mixture is filtered and evaporated to afford a yellow oil, that is chromatographed using methylene chloride to 92:8 methylene chloride:methanol in a gradient. The title compound is collected as a white solid weighing 12 mg (0.03 mmol, 18%). ES+(m/z)=476 [M+H]).

Workup

  1. stirringthe reaction mixture shaken at room temperature for 2 hr
  2. filtrationThe mixture is filtered
  3. customevaporated
  4. customto afford a yellow oil, that
  5. customis chromatographed
  6. customThe title compound is collected as a white solid

Sources & evidence

ORD record
ord-8e873a2ad60f44b492bf2c40d53c14ad
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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