HCID 70873131, compound → HCID 70874291, compound

HRID 1526126Notes

Reaction equation

HRID 1526126 reaction equation
[C:1]([C:3]1[C:4]([S:44][CH3:45])=[N:5][C:6]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[C:7]([C:31]([O:33]CC)=O)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH:11][C:10]=1[N+:28]([O-])=O)#[N:2]>C(O)(=O)C.[Fe]>[C:1]([C:3]1[C:4]([S:44][CH3:45])=[N:5][C:6]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[C:7]2[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]3)=[CH:11][C:10]=1[NH:28][C:31]2=[O:33])#[N:2]

Participants

4

Reactant 1

HCID 70873131HCID 70873131, compound

Product 1

HCID 70874291HCID 70874291, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

0.48 g (8.6 mmol) of iron is added to a solution of 1 g (1.7 mmol) of tert-butyl 4-(4-(3-cyano-5-(ethoxycarbonyl)-6-(4-methoxyphenyl)-2-(methylthio)pyridin-4-yl)-3-nitrophenyl)piperazine-1-carboxylate dissolved in 8.82 ml of acetic acid. The reaction medium is carried at 90° C. for 4 hours. The precipitate obtained is filtered on Dicalite and then rinsed with a 98:2 dichloroethane/methanol mixture. The filtrate is concentrated to yield 0.63 g (66%) of tert-butyl 4-(1-cyano-4-(4-methoxyphenyl)-2-(methylthio)-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)piperazine-1-carboxylate in the form of a yellow solid.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered on Dicalite
  3. washrinsed with a 98:2 dichloroethane/methanol mixture
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-82c2a5de6ccb4fcaa6d44aa5318ab2bc
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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