Triethylamine → HCID 71217376, compound

HRID 1887918Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-chloro-N-[7-fluoro-1-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-3-yl-methyl]-nicotinamide (55 mg, 0.129 mmol), piperidin-4-yl methanol (22.3 mg, 0.194 mmol), triethylamine (0.036 mL, 258 mmol), and DMF (2 mL) was heated in a sealed tube at 140° C. for 5 hr. The crude material was purified by reverse phase chromatography (10% acetonitrile-water ramped to 60% acetonitrile-water). The product 4-hydroxymethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid [7-fluoro-1-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-3-ylmethyl]-amide (25 mg, 38%) was isolated as a light yellow solid. MS calcd. for C28H26F2N4O3 [(M+H)+] 505.2, obsd. 505.1.

Workup

customThe crude material was purified by reverse phase chromatography (10% acetonitrile-water ramped to 60% acetonitrile-water)

Sources & evidence

ORD record: ord-d351d3e176544ba4a8dcf3baf4d018c0
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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