Acetonitrile → HCID 71209027, compound

HRID 1887885Notes

Reaction equation

Cl[C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][CH2:9][C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=3)[N:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=2)=[O:7])=[CH:4][N:3]=1.[C@H:30]12[CH2:36][C@H:33]([NH:34][CH2:35]1)[CH2:32][N:31]2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].C(N(CC)C(C)C)(C)C.CC#N>CN1C(=O)CCC1>[C:40]([O:39][C:37]([N:31]1[CH2:32][CH:33]2[CH2:36][CH:30]1[CH2:35][N:34]2[C:2]1[CH:29]=[CH:28][C:5]([C:6](=[O:7])[NH:8][CH2:9][C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=3)[N:12]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:11]=2)=[CH:4][N:3]=1)=[O:38])([CH3:43])([CH3:41])[CH3:42]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 6-chloro-N-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methyl)nicotinamide (intermediate E) (30 mg, 0.071 mmol), (1S,4S)-tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (43 mg, 0.212 mmol) and N,N-diisopropylethylamine (59.2 mg, 80.0 μL, 0.456 mmol) in NMP (500 μL) was stirred at 115° C. in a sealed tube overnight. The reaction mixture was transferred to a vial with CH3CN, then concentrated under a stream of nitrogen. The crude product was purified using preparative reverse-phase HPLC. The product 5-{5-[(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-carbamoyl]-pyridin-2-yl}-2,5-diaza-bicyclo-[2.2.1]-heptane-2-carboxylic acid tert-butyl ester (28 mg, 68%) was obtained as a white solid. MS calcd. for C32H32ClN5O4 [(M+H)+] 586.2, obsd. 586.0.

Workup

concentrationconcentrated under a stream of nitrogen
customThe crude product was purified

Sources & evidence

ORD record: ord-52c641a9dba64f9e87278236ad9c9635
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501732B2

Reaction notes

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