p-Toluenesulfonic acid → 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 4-methylbenzenesulfonate

HRID 222969Notes

Reaction equation

HRID 222969 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]([NH:34][CH:35]3[CH2:40][C:39]([CH3:42])([CH3:41])[NH:38][C:37]([CH3:44])([CH3:43])[CH2:36]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:45].[C:46]1([CH3:56])[CH:51]=[CH:50][C:49]([S:52]([OH:55])(=[O:54])=[O:53])=[CH:48][CH:47]=1>CC(O)C>[CH3:56][C:46]1[CH:47]=[CH:48][C:49]([S:52]([OH:55])(=[O:54])=[O:53])=[CH:50][CH:51]=1.[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:34][CH:35]3[CH2:36][C:37]([CH3:43])([CH3:44])[NH:38][C:39]([CH3:42])([CH3:41])[CH2:40]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:45]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 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-thiophenecarboxamide

Product 1

HCID 86608568N-(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 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Added IPA (5 mL) to 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 (203.2 mg) and heated to 60° C. Added p-toluenesulfonic acid (1.1 eq; 1M in water), and solution clarified. After a few minutes at about 60° C., cooled to rt. Stirred for about 3 hrs at rt, then filtered, washed with IPA, and dried in vacuum oven at 50° C. to provide the title compound (123.9 mg). Melting point (tested with DSC) is 335° C.

Workup

  1. waitAfter a few minutes at about 60° C.
  2. temperaturecooled to rt
  3. filtrationfiltered
  4. washwashed with IPA
  5. customdried in vacuum oven at 50° C.

Sources & evidence

ORD record
ord-5ff8030c943240fa8cf549d841770d94
Source dataset
uspto-grants-2012_06
Patent number
US08207176B2

Reaction notes

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