Chlorosuccinimide → HCID 86710352, compound

HRID 1398358Notes

Reaction equation

HRID 1398358 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]1[CH:14]=[C:15]([O:18][CH2:19][C@H:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:16]=[CH:17][C:7]2=1.C1C(=O)N([Cl:40])C(=O)C1>C(#N)C>[Cl:40][C:16]1[C:15]([O:18][CH2:19][C@H:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:14][C:8]2[N:9]([CH3:13])[C:10](=[O:12])[C:11]3[C:6]([C:7]=2[CH:17]=1)=[CH:5][CH:4]=[N:3][C:2]=3[CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86710351HCID 86710351, compound

Product 1

HCID 86710352HCID 86710352, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (R)-tert-butyl (1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (248 mg, 0.564 mmol) prepared as described in Example 19, Part A, NCS (151 mg, 1.128 mmol), and acetonitrile (5 mL) was heated at 90° C. for 1 h and then stirred at room temperature overnight. The crude material was concentrated under reduced pressure to afford (R)-tert-butyl (1-((9-chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (15 mg, 0.032 mmol, 6% crude yield). The mixture was carried on without further purification. LC/MS, (ESI) m/z 474.2 [(M+H)+, calcd for C25H33ClN3O4 474.2].

Workup

  1. customprepared
  2. concentrationThe crude material was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c529f3686c8435ebea50858d0e91ab1
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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