1-(Pyridin-2-ylmethyl)-1H-indazol-5-amine → tert-Butyl 3-cyano-4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

HRID 38569Notes

Reaction equation

HRID 38569 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.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][N:31]1[C:39]2[C:34](=[CH:35][C:36]([NH2:40])=[CH:37][CH:38]=2)[CH:33]=[N:32]1>>[C:8]([C:7]1[C:2]([NH:40][C:36]2[CH:35]=[C:34]3[C:39](=[CH:38][CH:37]=2)[N:31]([CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=2)[N:32]=[CH:33]3)=[C:3]2[C:16]3[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:11]=3[S:10][C:4]2=[N:5][CH:6]=1)#[N:9]

Participants

3

Reactant 2

HCID 219523661-(Pyridin-2-ylmethyl)-1H-indazol-5-amineHCID 58116935tert-Butyl 4-chloro-3-cyano-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Product 1

HCID 58116789tert-Butyl 3-cyano-4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}-5,8-dihydrothieno[2,3-b:5,4-c']dipyridine-7(6H)-carboxylate

Procedure

In analogy to Example 54A, the 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 (220 mg, 0.63 mmol) and 1-(pyridin-2-ylmethyl)-1H-indazol-5-amine from Example 61A (141 mg, 0.63 mmol) to yield 177 mg (52%).

Workup

  1. customto yield 177 mg (52%)

Sources & evidence

ORD record
ord-68c425605f9447d381e5ceb5f3e06bed
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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