Methyl 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylate → Methyl 2-(3-{[6-amino-5-(trifluoroacetyl)pyridin-2-yl]amino}piperidin-1-yl)-6-(2-methoxyphenyl)pyridine-3-carboxylate hydrochloride

HRID 1183011Notes

Reaction equation

HRID 1183011 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[N:3]=1.Cl.[NH2:21][C:22]1[C:27]([C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])=[CH:26][CH:25]=[C:24]([NH:34][CH:35]2[CH2:40][CH2:39][CH2:38][NH:37][CH2:36]2)[N:23]=1>>[ClH:1].[NH2:21][C:22]1[N:23]=[C:24]([NH:34][CH:35]2[CH2:40][CH2:39][CH2:38][N:37]([C:2]3[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[C:4]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[O:18][CH3:19])[N:3]=3)[CH2:36]2)[CH:25]=[CH:26][C:27]=1[C:28](=[O:33])[C:29]([F:32])([F:31])[F:30]

Participants

3

Reactant 2

HCID 58379299Methyl 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylateHCID 670602981-[2-Amino-6-(piperidin-3-ylamino)pyridin-3-yl]-2,2,2-trifluoroethanone hydrochloride

Product 1

HCID 67332827Methyl 2-(3-{[6-amino-5-(trifluoroacetyl)pyridin-2-yl]amino}piperidin-1-yl)-6-(2-methoxyphenyl)pyridine-3-carboxylate hydrochloride

Procedure

Analogously to the preparation of Example 8, 255 mg (0.84 mmol) of methyl 2-chloro-6-(2-methoxyphenyl)pyridine-3-carboxylate (Example 17A) and 299 mg (0.92 mmol) of 1-[2-amino-6-(piperidin-3-ylamino)pyridin-3-yl]-2,2,2-trifluoroethanone hydrochloride (Example 13A) were used to obtain, after purification of the crude product by means of preparative HPLC (method 10), 275 mg (58% of theory) of the product in solid form.

Workup

  1. customto obtain
  2. customafter purification of the crude product by means of preparative HPLC (method 10), 275 mg (58% of theory) of the product in solid form

Sources & evidence

ORD record
ord-ee37a331d82b495588d803a3162dd8d7
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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