Diethyl Ether → 4-(2-{[2-(2-Pyridylamino)ethyl]amino}pyrimidin-4-yl)benzamide

HRID 2228589Notes

Reaction equation

HRID 2228589 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.Cl[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(N)CN.N1[C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([C:31]([NH2:33])=[NH2+])[C:25]=2N=N1.CCN(C(C)C)C(C)C.CC[O:45]CC>C(#N)C>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][CH2:3][CH2:2][NH:1][C:12]1[N:17]=[C:16]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([NH2:33])=[O:45])=[CH:25][CH:26]=2)[CH:15]=[CH:14][N:13]=1

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 3301EthylenediamineHCID 744042-ChloropyrimidineHCID 81531DiisopropylethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 178512433HCID 178512433, compound

Product 1

HCID 221428344-(2-{[2-(2-Pyridylamino)ethyl]amino}pyrimidin-4-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2-Aminoethylamino)pyridine (prepared from 2-chloropyrimidine and ethylenediamine in accordance with the method described in T. Mega et al., 1988, Bull. Chem. Soc. Japan 61:4315, which is incorporated herein by reference) (6 mmol) was treated wit benzotriazole carboxamidinium 4-methylbenzenesulfonatesulfonate (2.0 g, 6 mmol) and DIEA (1.05 ml, 6 mmol) in anhydrous acetonitrile (10 ml) for 65 hours. Ether (ca. 10 ml) was then added to this mixture. After 8 hours the white solid amino[2-(2-pyridylamino)ethyl]carboxamidinium 4-methylbenzenesulfonate was filtered off and dried in vacuo. The resulting guanidine (200 mg) was reacted with 100 mg of resin (21 hours, 90° C.) according to the method described in Example 10 (Resin method C), to give the title compound.

Workup

  1. filtrationAfter 8 hours the white solid amino[2-(2-pyridylamino)ethyl]carboxamidinium 4-methylbenzenesulfonate was filtered off
  2. customdried in vacuo
  3. customThe resulting guanidine (200 mg) was reacted with 100 mg of resin (21 hours, 90° C.)

Sources & evidence

ORD record
ord-de212cc353e4461298ae8c67611ef103
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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