Methanol → HCID 58966972, compound

HRID 252632Notes

Reaction equation

HRID 252632 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[N:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[N:26]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:16][CH:17]=1)=[C:10]=S.N=C=N.CO>C1COCC1.ClCCl>[CH3:32][NH:31][C:27]1[N:26]=[C:25]([C:24]2[C:19]([O:18][C:15]3[N:16]=[CH:17][C:12]([NH:9][C:10]4[NH:8][C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=5[N:7]=4)=[CH:13][CH:14]=3)=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:30]=[CH:29][N:28]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7243O-PhenylenediamineHCID 160435CarbodiimideHCID 86614956HCID 86614956, compound

Product 1

HCID 58966972HCID 58966972, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzene-1,2-diamine (0.091 g, 0.85 mmol), 4-(2-(5-isothiocyanatopyridin-2-yloxy)pyridin-3-yl)-N-methylpyrimidin-2-amine (0.237 g, 0.70 mmol), and polymer-supported carbodiimide (Argonaut technologies, 1.6 mmol/g, 1.3 g, 2.1 mmol) was heated for 14 h in anhydrous THF in a sealed vial. The reaction was cooled and was filtered, rinsing with 100 mL DCM. The filtrate was concentrated in vacuo to give an off-white solid. Sonication in dichloromethane gave a fluffy precipitate, which was filtered and collected to give an off-white solid. This material was adsorbed onto 0.8 g SiO2 from MeOH/MC, and purified by silica gel chromatography, 40 g, 0-10% MeOH/MC to give N-(6-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)pyridin-3-yl)-1H-benzo[d]imidazol-2-amine as a white solid MS m/z=411 [M+H]+. Calc'd for C22H18N8O: 410.4.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationwas filtered
  3. washrinsing with 100 mL DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give an off-white solid
  6. customgave a fluffy precipitate, which
  7. filtrationwas filtered
  8. customcollected
  9. customto give an off-white solid
  10. custompurified by silica gel chromatography, 40 g, 0-10% MeOH/MC

Sources & evidence

ORD record
ord-f6bae8ed3007447798e741afba8885fe
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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