p-Toluenesulfonic acid → 2-[4-(tert-Butyldimethylsilanyloxy)phenyl]-1-(2-chloro-4-fluorophenyl)-3-methyl-5-piperidin-1-yl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

HRID 2102865Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH:16]([C:18]2[C:19](=[O:39])[N:20]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:21][CH2:22][C:23]=2[NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[Cl:32])[CH3:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[Cl:32])[C:23]3[CH2:22][CH2:21][N:20]([N:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)[C:19](=[O:39])[C:18]=3[C:16]=2[CH3:17])=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

3-{2-[4-(tert-Butyldimethylsilanyloxy)phenyl]-1-methyl-2-oxo-ethyl} -4-(2-chloro-4-fluorophenylamino)-5,6,3′,4′,5′,6′-hexahydro-2′H-[1,1′]bipyridinyl-2-one (1.135 g, 1.94 mmol) was suspended in toluene (5 ml) and toluene-4-sulfonic acid (0.037 g, 0.19 mmol) was added. The reaction mixture was heated in a microwave oven at 100° C. for 30 min. Water/toluene were added to the reaction mixture and the phases separated. The organic phase was washed with water, dried (MgSO4), filtered and evaporated to yield the crude product (crude 0.929 g).

Workup

customthe phases separated
washThe organic phase was washed with water
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-0b96953b8fa542a2b08211bfa725582d
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576095B2

Reaction notes

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