3-(Ethylamino)azetidine-3-carboxamide → 1-(6-(2-Chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-3-(ethylamino)azetidine-3-carboxamide

HRID 1867872Notes

Reaction equation

HRID 1867872 reaction equation
ClC1N2N=C(C3C=CC=CC=3Cl)C(C3C=CC(Cl)=CC=3)=CC2=NN=1.C(NC1(C(N)=O)CNC1)C.[Cl:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[C:43]([C:62]2[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=2)=[CH:44][C:45]2[N:46]([C:48]([N:51]3[CH2:55]C[C:53]([NH:59][CH2:60][CH3:61])([C:56]([NH2:58])=[O:57])[CH2:52]3)=[N:49][N:50]=2)[N:47]=1>>[Cl:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[C:43]([C:62]2[CH:67]=[CH:66][C:65]([Cl:68])=[CH:64][CH:63]=2)=[CH:44][C:45]2[N:46]([C:48]([N:51]3[CH2:52][C:53]([NH:59][CH2:60][CH3:61])([C:56]([NH2:58])=[O:57])[CH2:55]3)=[N:49][N:50]=2)[N:47]=1

Participants

4

Reactant 3

HCID 112865313-(Ethylamino)azetidine-3-carboxamideHCID 119930161-(6-(2-Chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-3-(ethylamino)pyrrolidine-3-carboxamideHCID 579797573-Chloro-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 119930171-(6-(2-Chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-3-(ethylamino)azetidine-3-carboxamideYield 32%

Procedure

The title compound (70 mg, 32%) as a yellow powder was prepared from 3-chloro-6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazine (168 mg, 0.45 mmol) and 3-(ethylamino)azetidine-3-carboxamide (291 mg, 1.35 mmol) in a manner analogous to that in which 1-(6-(2-chlorophenyl)-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-3-(ethylamino)pyrrolidine-3-carboxamide was prepared. HPLC/MS (method A): retention time=2.76 min, (M+H)+=482.2. 1H NMR (DMSO-d6, 400 MHz): δ 8.19 (s, 1H), 7.59-7.64 (m, 1H), 7.39-7.48 (m, 3H), 7.28-7.37 (m, 3H), 7.17-7.25 (m, 3H), 4.44 (d,J=8.07 Hz, 2H), 4.08 (d,J=8.07 Hz, 2H), 2.84 (bs, 1H), 2.41 (m, 2H), 1.02 (t, J=7.09 Hz, 3H).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-84f4274ba4ea43acb3b7060a26cc5767
Source dataset
uspto-grants-2009_12
Patent number
US07632837B2

Reaction notes

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