4-Amino-1,2,2,6,6-pentamethylpiperidine → 4-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-hydroxybenzamide

HRID 1352664Notes

Reaction equation

HRID 1352664 reaction equation
[Cl:1][C:2]1[C:21]([Cl:22])=[CH:20][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][C:10]=3[O:18]C)[NH:8][C:4]=2[CH:3]=1.ClC1C(Cl)=CC2N=C(C3C=CC(C(O)=O)=CC=3O)NC=2C=1.Cl.CN(C)CCCN=C=NCC.[CH3:56][N:57]1[C:62]([CH3:64])([CH3:63])[CH2:61][CH:60]([NH2:65])[CH2:59][C:58]1([CH3:67])[CH3:66]>C1COCC1>[Cl:22][C:21]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([NH:65][CH:60]4[CH2:59][C:58]([CH3:66])([CH3:67])[N:57]([CH3:56])[C:62]([CH3:64])([CH3:63])[CH2:61]4)=[O:17])=[CH:11][C:10]=3[OH:18])[NH:6][C:5]=2[CH:20]=1

Participants

6

Reactant 4

HCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211011665,6-Dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazoleHCID 1360923525,6-Dichloro-2-(4-carboxy-2-hydroxyphenyl)benzimidazole

Product 1

HCID 1354840234-(5,6-Dichlorobenzimidazol-2-yl)-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-3-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5,6-dichloro-2-(4-carboxy-2-methoxyphenyl)benzimidazole and 5,6-dichloro-2-(4-carboxy-2-hydroxyphenyl)benzimidazole (0.5 g, 1.48 mmol), prepared as described in Preparation 3,1-hydroxybenzotriazole (0.21 g, 1.56 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.35 g, 1.82 mmol) in THF (20 ml) was refluxed for 5 h. A solution of 1,2,2,6,6-pentamethyl-4-aminopiperidine (0.25 g, 1.5 mmol) in THF (3 ml) was added dropwise and refluxed for 3 h. After cooling to room temperature the solvent was evaporated under vacuum and the crude residue was purified by column chromatography eluting with CH2Cl2/MeOH/NH4OH 86:10:0.6 to give 10 mg of the title compound, mp>250° C.

Workup

  1. temperaturewas refluxed for 5 h
  2. temperaturerefluxed for 3 h
  3. customwas evaporated under vacuum
  4. customthe crude residue was purified by column chromatography
  5. washeluting with CH2Cl2/MeOH/NH4OH 86:10:0.6

Sources & evidence

ORD record
ord-92945c42d4f743c19499eda404d130b5
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

Loading…