3,4-Dichloroaniline → tert-Butyl 3-cyano-4-[(3,4-dichlorophenyl)amino]-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

HRID 38567Notes

Reaction equation

HRID 38567 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl[C:11]1[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]2[S:19][C:20]3[CH2:21][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][CH2:24][C:25]=3[C:12]=12>>[C:17]([C:16]1[C:11]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=2)=[C:12]2[C:25]3[CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][C:20]=3[S:19][C:13]2=[N:14][CH:15]=1)#[N:18]

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 58116935tert-Butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Product 1

HCID 58116901tert-Butyl 3-cyano-4-[(3,4-dichlorophenyl)amino]-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Procedure

In analogy to Example 54A, the title compound was synthesized from 3,4-dichloroaniline (116 mg, 0.72 mmol) and tert-butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c′]dipyridine-7(6H)-carboxylate (250 mg, 0.72 mmol) from Example 53A to yield 207 mg (61%).

Workup

  1. customto yield 207 mg (61%)

Sources & evidence

ORD record
ord-05b2a9b1c1a94a60acf4855a63862b75
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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