N3-(4-methoxybenzoyl)-3,4-pyridinediamine → N4-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

HRID 1445436Notes

Reaction equation

HRID 1445436 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:28][O:29][C:30]1[CH:45]=[CH:44][C:33]([C:34]([NH:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][C:42]=2[NH2:43])=[O:35])=[CH:32][CH:31]=1>>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[C:22]([C:24]([CH3:26])([CH3:25])[CH3:27])[CH:21]=[CH:20][C:16]=2[C:17]([NH:43][C:42]2[CH:41]=[CH:40][N:39]=[CH:38][C:37]=2[NH:36][C:34](=[O:35])[C:33]2[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:45][CH:44]=2)=[O:19])[CH2:10][CH2:9]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 12069538N3-(4-methoxybenzoyl)-3,4-pyridinediamineHCID 685305052-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid

Product 1

HCID 69492771N4-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

Procedure

Using methods substantially equivalent to those described in Example 101-D, 2-(N-Boc-piperidine-4-yloxy)-4-(tert-butyl)benzoic acid (1.0 g, 2.65 mmol) is converted into the acid chloride and used to acylate N3-(4-methoxybenzoyl)-3,4-pyridinediamine (600 mg, 2.47 mmol). After purification by chromatography (SiO2: 30% to 50% EtOAc in chloroform) 589 mg (40%) of the title compound is obtained.

Workup

  1. customAfter purification by chromatography (SiO2: 30% to 50% EtOAc in chloroform) 589 mg (40%) of the title compound
  2. customis obtained

Sources & evidence

ORD record
ord-9b6003131ca54a2cad14e1c2add5c747
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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