2-amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamide → N-(5-Chloropyridin-2-yl)-5-fluoro-2-[4-isopropyl-2-(piperidin-3-yl-methoxy)benzoylamino]benzamide Dihydrochloride

HRID 644240Notes

Reaction equation

HRID 644240 reaction equation
Cl.[CH:2]([C:5]1[CH:30]=[CH:29][C:8]([C:9]([NH:11][C:12]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:10])=[C:7]([O:31][CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]2)[CH:6]=1)([CH3:4])[CH3:3].C(C1C=CC(C(O)=O)=C(OCC2CCCN(C(OC(C)(C)C)=O)C2)C=1)(C)C.[Cl:66]C1C=CC(NC(=O)C2C=C(F)C=CC=2N)=NC=1>>[ClH:23].[ClH:66].[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:12]=2[NH:11][C:9](=[O:10])[C:8]2[CH:29]=[CH:30][C:5]([CH:2]([CH3:4])[CH3:3])=[CH:6][C:7]=2[O:31][CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]2)=[N:18][CH:19]=1

Participants

4

Reactant 3

HCID 219063152-amino-N-(5-chloropyridin-2-yl)-5-fluorobenzamideHCID 685322644-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acidHCID 685711222-[4-isopropyl-2-(piperidin-3-yl-methoxy)benzoylamino]-N-(5-chloropyridin-2-yl)-5-fluorobenzamide hydrochloride

Product 1

HCID 68572225N-(5-Chloropyridin-2-yl)-5-fluoro-2-[4-isopropyl-2-(piperidin-3-yl-methoxy)benzoylamino]benzamide Dihydrochloride

Procedure

Using methods substantially equivalent to those described in example 60-I & J, 2-[4-isopropyl-2-(piperidin-3-yl-methoxy)benzoylamino]-N-(5-chloropyridin-2-yl)-5-fluorobenzamide hydrochloride (92 mg, 0.15 mmol, 14%) was prepared from 4-isopropyl-2-(N-tert-butoxycarbonylpiperidin-3-yl)methoxybenzoic acid and N-(5-chloropyridin-2-yl)-2-amino-5-fluorobenzamide after reverse phase HPLC purification.

Workup

  1. customafter reverse phase HPLC purification

Sources & evidence

ORD record
ord-aec0412a1c234dad84c724310f307f2b
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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