1-((4'-Chlorobiphenyl-2-yl)methyl)-3-fluoropiperidin-4-one → N-(7-(1((4'-Chlorobiphenyl-2-yl)methyl)-3-fluoropiperidin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide

HRID 2406244Notes

Reaction equation

HRID 2406244 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C@@H:9]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]3[C:30]4[CH2:38][CH2:37][NH:36][CH2:35][C:31]=4[N:32]=[CH:33][N:34]=3)(=[O:27])=[O:26])=[CH:21][C:20]=2[S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40])[CH2:10][S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:2]1.[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[CH2:59][N:60]2[CH2:65][CH2:64][C:63](=O)[CH:62]([F:67])[CH2:61]2)=[CH:49][CH:48]=1>>[Cl:46][C:47]1[CH:52]=[CH:51][C:50]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=2[CH2:59][N:60]2[CH2:65][CH2:64][CH:63]([N:36]3[CH2:37][CH2:38][C:30]4[C:29]([NH:28][S:25]([C:22]5[CH:23]=[CH:24][C:19]([NH:18][C@H:9]([CH2:8][CH2:7][N:4]6[CH2:5][CH2:6][O:1][CH2:2][CH2:3]6)[CH2:10][S:11][C:12]6[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=6)=[C:20]([S:39]([C:42]([F:43])([F:44])[F:45])(=[O:41])=[O:40])[CH:21]=5)(=[O:27])=[O:26])=[N:34][CH:33]=[N:32][C:31]=4[CH2:35]3)[CH:62]([F:67])[CH2:61]2)=[CH:49][CH:48]=1

Participants

3

Reactant 2

HCID 670544011-((4'-Chlorobiphenyl-2-yl)methyl)-3-fluoropiperidin-4-oneHCID 67980912(R)-4-(4-Morpholino-1-(phenylthio)butan-2-ylamino)-N-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-(trifluoromethylsulfonyl)benzenesulfonamide

Product 1

HCID 86667198N-(7-(1((4'-Chlorobiphenyl-2-yl)methyl)-3-fluoropiperidin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamideYield 12.1%

Procedure

Following General Reductive Amination Procedure 2, (R)-4-(4-Morpholino-1-(phenylthio)butan-2-ylamino)-N-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-(trifluoromethylsulfonyl)benzenesulfonamide (34 mg, 0.05 mmol) and 1-((4′-chlorobiphenyl-2-yl)methyl)-3-fluoropiperidin-4-one (19 mg, 0.059 mmol) afforded the title compound (6 mg, 12% yield).

Sources & evidence

ORD record
ord-90c498e0f98b4368bc2b1516862a243d
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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