4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine → 4-(4,5-dimethylthiophen-2-yl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine

HRID 503544Notes

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[S:13][C:14]([CH3:18])=[C:15]([CH3:17])[CH:16]=2)=[N:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=3)=[CH:26][CH:27]=[N:28]2)=[N:23][CH:22]=1>C(O)(C)(C)C>[CH3:17][C:15]1[CH:16]=[C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([NH:38][C:35]3[CH:34]=[CH:33][C:32]([O:31][C:25]4[C:24]5[C:29](=[CH:30][C:21]([O:20][CH3:19])=[CH:22][N:23]=5)[N:28]=[CH:27][CH:26]=4)=[CH:37][CH:36]=3)=[N:3][N:4]=2)[S:13][C:14]=1[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

In a nitrogen purged sealed tube, 1-chloro-4-(4,5-dimethylthiophen-2-yl)phthalazine (0.040 g, 0.146 mmol) was dissolved in tert-butanol (1.00 mL). 4-(7-Methoxy-1,5-naphthyridin-4-yloxy)benzenamine (0.039 g, 0.146 mmol) was added, and the reaction mixture in the tube was stirred at 100° C. for 3 h. The mixture was concentrated in vacuo, and the crude material was purified by silica gel chromatography using 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2. Product-containing fractions were concentrated to yield 4-(4,5-dimethylthiophen-2-yl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine as light yellow solid. MS [N+H]=506.0; Calc'd 505.6 for C29H23N5O2S.

Workup

customIn a nitrogen purged
customsealed tube
concentrationThe mixture was concentrated in vacuo
customthe crude material was purified by silica gel chromatography
concentrationProduct-containing fractions were concentrated

Sources & evidence

ORD record: ord-1b7a385518344524b3068641746bb65f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776857B2

Reaction notes

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