Tert-Butyl-[5''-(3-methoxy-phenyl)-[2,2';4',3'']terpyridin-6'-yl]-amine → 5''-(3-Methoxy-phenyl)-[2,2';4',3'']terpyridin-6'-ylamine

HRID 1798495Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Tert-Butyl-[5″-(3-methoxy-phenyl)-[2,2′;4′,3″]terpyridin-6′-yl]-amine (1 eq, 0.073 mmol, 0.030 g) is dissolved in TFA (6 ml)/DCM (1 ml) and the reaction mixture is heated at 70° C. for 5 hours. The reaction mixture is cooled down and reduced in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 355.

Workup

temperatureThe reaction mixture is cooled down
washeluting with MeOH
concentrationconcentrated in vacuo
customdried under vacuum

Sources & evidence

ORD record: ord-9a57e2d39c1f4cbb98d2b27e7b90135d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343966B2

Reaction notes

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