(2,6-Dichlorophenyl)hydrazine monohydrochloride → 2-(2,6-Dichlorophenyl)-2,8-dihydropyrazolo[3,4-d]dipyrido[2,3-b:3',4'-f]azepine

HRID 1043493Notes

Reaction equation

HRID 1043493 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][NH2:11].CN([CH:15]=[C:16]1[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:21]=2[NH:20][C:19]2[N:27]=[CH:28][CH:29]=[CH:30][C:18]=2[C:17]1=O)C>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[N:10]1[CH:15]=[C:16]2[C:17]([C:18]3[CH:30]=[CH:29][CH:28]=[N:27][C:19]=3[NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=32)=[N:11]1

Participants

4

Reactant 2

HCID 2723909(2,6-Dichlorophenyl)hydrazine monohydrochlorideHCID 668865836-[(Dimethylamino)methylene]-6,11-dihydro-5H-dipyrido[2,3-b: 3',4'-f]azepin-5-one

Product 1

HCID 1354108982-(2,6-Dichlorophenyl)-2,8-dihydropyrazolo[3,4-d]dipyrido[2,3-b:3',4'-f]azepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2,6-Dichlorophenyl)hydrazine hydrochloride (168 mg, 0.788 mmol) was added to a solution of 6-[(dimethylamino)methylene]-6,11-dihydro-5H-dipyrido[2,3-b:3′,4′-f]azepin-5-one (105 mg, 0.394 mmol, Intermediate E-1) in ethanol (4 mL) and stirred at room temperature. After 30 minutes, the mixture was heated to 60° C. overnight. The reaction was then cooled to room temperature and the major product from the reaction mixture was isolated using preparative LC/MS to provide the desired product as a white powder. 1H NMR (DMSO-d6) δ 8.77 (bs, 1H), 8.45 (bs, 1H), 8.40 (bs, 1H), 8.04 (m, 2H), 7.94 (d, 1H), 7.75 (m, 2H), 7.62 (m, 1H), 6.95 (m, 1H), 6.87 (m, 1H). LC/MS: 380 (M+H)+.

Workup

  1. temperaturethe mixture was heated to 60° C. overnight
  2. temperatureThe reaction was then cooled to room temperature
  3. customthe major product from the reaction mixture was isolated

Sources & evidence

ORD record
ord-2eacae2ddddd4258ac1e45048c35f729
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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