2-Amino-5-methylpyridine → HCID 59560177, compound

HRID 1643824Notes

Reaction equation

HRID 1643824 reaction equation
[Cl-].C[Al+]C.[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.C[O:14][C:15]([C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][C:23]([CH3:28])([CH3:27])[O:24]2)=[C:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[CH:18]=1)=O.C[O:39][C:40]([C:42]1[C:43]2[CH2:44][CH2:45][C:46]([CH3:62])([CH3:61])[O:47][C:48]=2[CH:49]=[C:50]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=2[Cl:60])[CH:51]=1)=O>>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:15]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][C:23]([CH3:28])([CH3:27])[O:24]3)=[C:19]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[CH:18]=2)=[O:14])=[N:10][CH:11]=1.[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:40]([C:42]2[C:43]3[CH2:44][CH2:45][C:46]([CH3:62])([CH3:61])[O:47][C:48]=3[CH:49]=[C:50]([O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=3[Cl:60])[CH:51]=2)=[O:39])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 153482-Amino-5-methylpyridineHCID 16686359Dimethylalumanylium chlorideHCID 59560137HCID 59560137, compoundHCID 59560275HCID 59560275, compound

Product 2

HCID 59559958HCID 59559958, compoundYield 10%HCID 59560177HCID 59560177, compoundYield 23%

Procedure

The title compound was prepared in a similar manner as described for Example 1, from dimethylaluminum chloride (1.0 M in hexanes, 2.9 mL, 2.9 mmol), 5-methyl-2-aminopyridine (314 mg, 2.9 mmol), and a mixture of 5-(2-chloro-benzyloxy)-2,2-dimethyl-chroman-7-carboxylic acid methyl ester and 7-(2-chloro-benzyloxy)-2,2-dimethyl-chroman-5-carboxylic acid methyl ester (374c) (crude 104 mg). Purification by reverse phase chromatography gave 5-(2-chloro-benzyloxy)-2,2-dimethyl-chroman-7-carboxylic acid(5-methyl-pyridin-2-yl)-amide (374) (11 mg, 10% yield) and 7-(2-chloro-benzyloxy)-2,2-dimethyl-chroman-5-carboxylic acid(5-methyl-pyridin-2-yl)-amide (375) as a white solid (25 mg, 23% yield).

Workup

  1. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-e1f1a7f09b984d7581d6b878416376a6
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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