3-Chloro-4-(2-pyridylmethoxy)aniline → tert-Butyl 4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

HRID 38543Notes

Reaction equation

HRID 38543 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[S:10][C:11]3[CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][C:16]=3[C:3]=12.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)[NH2:28]>>[Cl:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[S:10][C:11]4[CH2:12][N:13]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:14][CH2:15][C:16]=4[C:3]=23)[CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1

Participants

3

Reactant 2

HCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 58116935tert-Butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Product 1

HCID 58116804tert-Butyl 4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylateYield 64%

Procedure

In analogy to Example 54A, the title compound was synthesized from tert-butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c′]dipyridine-7(6H)-carboxylate from Example 53A (190 mg, 0.54 mmol) and 3-chloro-4-(pyridin-2-ylmethoxy)aniline from Example 6A (127 mg, 0.54 mmol) to yield 215 mg (88% purity, 64% yield), which were used without further purification.

Workup

  1. customto yield 215 mg (88% purity, 64% yield), which
  2. customwere used without further purification

Sources & evidence

ORD record
ord-b9c17ffcb88e4f9fb2c1b24e253582ad
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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