4-Piperidinemethanol → 4-hydroxymethyl-3,4,5,6-tetrahydro-2H[1,2']bipyridinyl-5'-carboxylic acid (7-chloro-2-dimethylcarbamoyl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide

HRID 1887852Notes

Reaction equation

[CH3:1][N:2]([CH3:34])[C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][NH:16][C:17]([C:19]1[CH:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1)=[O:18])=[CH:11][CH:10]=[C:9]([Cl:27])[CH:8]=2)=[O:4].[NH:35]1[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]1>CN1C(=O)CCC1>[Cl:27][C:9]1[CH:8]=[C:7]2[C:12]([C:13](=[O:26])[C:14]([CH2:15][NH:16][C:17]([C:19]3[CH:24]=[CH:23][C:22]([N:35]4[CH2:40][CH2:39][CH:38]([CH2:41][OH:42])[CH2:37][CH2:36]4)=[N:21][CH:20]=3)=[O:18])=[C:5]([C:3](=[O:4])[N:2]([CH3:1])[CH3:34])[N:6]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 125 °C

Procedure

The intermediate 7-chloro-3-{[(6-chloro-pyridine-3-carbonyl)-amino]-methyl}-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (70 mg, 0.141 mmol) was combined with piperidin-4-ylmethanol (40 mg, 0.346 mmol) and NMP (2 mL). The reaction mixture was heated at 125° C. for 2 hr. After this time, the crude product was subjected to preparative reverse-phase HPLC purification. The product, 4-hydroxymethyl-3,4,5,6-tetrahydro-2H[1,2′]bipyridinyl-5′-carboxylic acid (7-chloro-2-dimethylcarbamoyl-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-amide was obtained as 30 mg (37%) of a white solid. MS calcd. for C31H32ClN5O4 [(M+H)+] 574.2, obsd. 574.3.

Workup

customAfter this time, the crude product was subjected to preparative reverse-phase HPLC purification

Sources & evidence

ORD record: ord-fcd5459c231d4cd9b7cb16ab2d3e4a8a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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