2-Chlorobenzothiazole → 6-(Benzothiazol-2-ylamino)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796612Notes

Reaction equation

HRID 1796612 reaction equation
Cl.[NH2:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1.Cl[C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1>CN(C=O)C>[S:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[NH:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1

Participants

4

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 221794876-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride

Product 1

HCID 221794936-(Benzothiazol-2-ylamino)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Amino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile hydrochloride (9.5 mg, 0.024 mmol) and 2-chlorobenzothiazole (4.4 mg, 0.026 mmol) in DMF (0.1 ml) were stirred at 100° C. for 12 hrs. The reaction mixture was concentrated and purified by silica gel flash chromatography to isolate 379 as a yellow film (3.3 mg, 28%). [M+H]+489.14

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-df0703e65ada4e15b485518857a50369
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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