Thionyl Chloride → N-(5-Chloropyridin-2-yl)-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]-4-methoxycarbonylbenzamide

HRID 1247167Notes

Reaction equation

HRID 1247167 reaction equation
N1C=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]2)=[CH:3]C=1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:36]=[C:35]([C:37]([O:39][CH3:40])=[O:38])[CH:34]=[CH:33][C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=1)=[O:24]>>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:23](=[O:24])[C:22]2[CH:33]=[CH:34][C:35]([C:37]([O:39][CH3:40])=[O:38])=[CH:36][C:21]=2[NH:20][C:13]([CH:10]2[CH2:9][CH2:8][N:7]([CH:4]([CH3:3])[CH3:5])[CH2:12][CH2:11]2)=[O:15])=[N:27][CH:28]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acidHCID 219063182-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

Product 1

HCID 21906664N-(5-Chloropyridin-2-yl)-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]-4-methoxycarbonylbenzamide

Procedure

Using a similar procedure to that described in Example 275, 1-(4-pyridinyl)piperidin-4-ylcarboxylic acid (2.0 g, 9.7 mmol), thionyl chloride (1.4 mL, 19 mmol), and 2-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide (2.8 g, 9.2 mmol) afforded, after purification by column chromatography (SiO2: 5 to 10% [2.0 N ammonia in methanol]:methylene chloride), 0.40 g (9%) of the title compound.

Workup

  1. customafforded
  2. customafter purification by column chromatography (SiO2: 5 to 10% [2.0 N ammonia in methanol]:methylene chloride), 0.40 g (9%) of the title compound

Sources & evidence

ORD record
ord-3132502bf3aa40e08785e484260b187c
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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