4-Amino-2,2,6,6-tetramethylpiperidine → N-(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-methylphenyl)-3-thiophenecarboxamide

HRID 1806550Notes

Reaction equation

HRID 1806550 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](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:38].[CH3:39][C:40]1([CH3:49])[CH2:45][CH:44]([NH2:46])[CH2:43][C:42]([CH3:48])([CH3:47])[NH:41]1>C(#N)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:46][CH:44]3[CH2:45][C:40]([CH3:49])([CH3:39])[NH:41][C:42]([CH3:48])([CH3:47])[CH2:43]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([NH:26][C:27]([C:29]4[CH:33]=[CH:32][S:31][CH:30]=4)=[O:28])[CH:22]=[CH:23][C:24]=3[CH3:25])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:38]

Participants

4

Reactant 2

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 11947980N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylphenyl}-3-thiophenecarboxamide

Product 1

HCID 11947981N-(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-methylphenyl)-3-thiophenecarboxamideYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from N-{3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methylphenyl}-3-thiophenecarboxamide and 2,2,6,6-tetramethyl-4-piperidinamine according to General Procedure for Sulfoxide/Sulfone Displacement, described above. The concentrated reaction mixture was slurried with acetonitrile and filtered. The solid was recrystallized from methanol/water to afford the desired product as a crystalline solid (0.2 g, 16%). HPLC indicated >99% pure: LC-MS m/z 629 (M+H)+, 1.86 min (ret time).

Workup

  1. customThe concentrated reaction mixture
  2. filtrationfiltered
  3. customThe solid was recrystallized from methanol/water

Sources & evidence

ORD record
ord-315391da08054374b6839e9046302d5f
Source dataset
uspto-grants-2013_01
Patent number
US08354416B2

Reaction notes

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