Phenethylamine → 3-{8-(2,6-difluorophenyl)-7-oxo-2-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-(2-phenylethyl)benzamide

HRID 222963Notes

Reaction equation

HRID 222963 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](SC)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([OH:24])=O)[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31].[C:32]1([CH2:38][CH2:39][NH2:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH3:41][C:42]1([CH3:51])[CH2:47][CH:46]([NH2:48])[CH2:45][C:44]([CH3:50])([CH3:49])[NH:43]1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:48][CH:46]3[CH2:47][C:42]([CH3:51])([CH3:41])[NH:43][C:44]([CH3:50])([CH3:49])[CH2:45]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=3[CH3:28])[C:22]([NH:40][CH2:39][CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:24])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:31]

Participants

4

Reactant 3

HCID 1001PhenethylamineHCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 575305303-[8-(2,6-Difluorophenyl)-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid

Product 1

HCID 119479383-{8-(2,6-difluorophenyl)-7-oxo-2-[(2,2,6,6-tetramethyl-4-piperidinyl)amino]-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-(2-phenylethyl)benzamide

Procedure

The title compound is prepared from 3-[8-(2,6-difluorophenyl)-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylbenzoic acid by following the procedures in Example 19 using 2-phenylethanamine for the amide formation and 2,2,6,6-tetramethyl-4-piperidinamine for the displacement reaction: LC-MS m/z 651 (M+H)+, 1.87 min (ret time).

Workup

  1. customfor the displacement reaction
  2. customLC-MS m/z 651 (M+H)+, 1.87 min (ret time)

Sources & evidence

ORD record
ord-293ffe879c4142bb8a50f57c9c4a2af2
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

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