p-Toluenesulfonic acid monohydrate → N-(4-(1,5-naphthyridin-4-ylthio)phenyl)-4-(4-chlorophenyl)phthalazin-1-amine

HRID 503543Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N:31]1[C:40]2[C:35](=[N:36][CH:37]=[CH:38][CH:39]=2)[C:34]([S:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)=[CH:33][CH:32]=1>C(O)(C)(C)C>[N:31]1[C:40]2[C:35](=[N:36][CH:37]=[CH:38][CH:39]=2)[C:34]([S:41][C:42]2[CH:47]=[CH:46][C:45]([NH:48][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]([C:12]4[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=4)=[N:4][N:3]=3)=[CH:44][CH:43]=2)=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-Chloro-4-(4-chlorophenyl)phthalazine (30 mg, 109 μmol), p-toluenesulfonic acid monohydrate (10 mg, 55 μmol) and 4-(1,5-naphthyridin-4-ylthio)benzenamine (33 mg, 131 μmol) were combined in t-butanol in a sealed tube and the reaction mixture was stirred at 100° C. for 2 h. The mixture was concentrated in vacuo and the crude material was purified by silica gel chromatography (0 to 100% 90/10/1 CH2Cl2/MeOH/NH4OH) in CH2Cl2. The material was further purified by silica gel chromatography (0 to 100% EtOAc/hexane) to afford N-(4-(1,5-naphthyridin-4-ylthio)phenyl)-4-(4-chlorophenyl)phthalazin-1-amine. MS [M+H]=492; Calc'd 491.99 for C28H18ClN5S.

Workup

concentrationThe mixture was concentrated in vacuo
customthe crude material was purified by silica gel chromatography (0 to 100% 90/10/1 CH2Cl2/MeOH/NH4OH) in CH2Cl2
customThe material was further purified by silica gel chromatography (0 to 100% EtOAc/hexane)

Sources & evidence

ORD record: ord-50fe5bcdf8c946f7b65af863e17c1afd
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776857B2

Reaction notes

Loading…