6-Chloro-3-nitropyridin-2-ylamine → HCID 22142787, compound

HRID 2297219Notes

Reaction equation

HRID 2297219 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:7][N:6]=1.Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29]([NH2:36])[N:28]=1>CO.C(Cl)Cl>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:9]1[C:8]([CH2:19][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:7][N:6]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[C:29]([NH2:36])[N:28]=2)[N:10]=1

Participants

4

Reactant 2

HCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 22143084(2-Aminoethyl)[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amine

Product 1

HCID 22142787HCID 22142787, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Using the conditions described in Example 139, (2-aminoethyl)[4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]amine and 10.6 mg (0.061 mmol) of 2-chloro-5-nitro-6-aminopyridine afforded 191 mg (60%) of [4-(2,4-dichlorophenyl)-5-(morpholin-4-ylmethyl)pyrimidin-2-yl]{2-[(5-nitro-6-amino(2-pyridyl))amino]ethyl}amine as a yellow solid following chromatography (silica gel, 5% methanol/methylene chloride).

Sources & evidence

ORD record
ord-8b13b60295db405da49568b0ac03c405
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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