Trifluoroacetic acid → 4-{2-[1-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide

HRID 2370485

반응식

HRID 2370485 반응식
O1C2C=CC=C(C=O)C=2OCC1.O1C2C=CC=C(C=N)C=2OCC1.C[Mg]Br.[O:28]1[C:33]2[CH:34]=[CH:35][CH:36]=[C:37]([CH:38]([NH2:40])[CH3:39])[C:32]=2[O:31][CH2:30][CH2:29]1.FC(F)(F)C(O)=O.[CH3:48][NH:49][C:50]([C:52]1[CH:57]=[C:56]([O:58][C:59]2[CH:70]=[CH:69][C:62]3[N:63]=[C:64](S(C)=O)[O:65][C:61]=3[CH:60]=2)[CH:55]=[CH:54][N:53]=1)=[O:51]>>[CH3:48][NH:49][C:50]([C:52]1[CH:57]=[C:56]([O:58][C:59]2[CH:70]=[CH:69][C:62]3[N:63]=[C:64]([NH:40][CH:38]([C:37]4[C:32]5[O:31][CH2:30][CH2:29][O:28][C:33]=5[CH:34]=[CH:35][CH:36]=4)[CH3:39])[O:65][C:61]=3[CH:60]=2)[CH:55]=[CH:54][N:53]=1)=[O:51]

참가 물질

7

반응물 6

HCID 6422Trifluoroacetic acidHCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehydeHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamideHCID 577255011-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamine3회HCID 86618567C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine2회HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 577255794-{2-[1-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide

실험 절차

An amine linked to a resin is reacted with 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde, thus giving C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine. C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine is derivatized with alkylation at the imino site, such as with methyl magnesium bromide. Other alkylating agents can be used according to the desired molecule. The resulting 1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-ethylamine is cleaved from the resin. An example of a resin-cleaving agent is trifluoroacetic acid (TFA). The resulting 1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-ethylamine can be used for synthesis of a compound of the embodiments. For instance, 1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-ethylamine can be used to react with 4-(2-methanesulfinyl-benzooxazol-6-yloxy)-pyridine-2-carboxylic acid methylamide to form 4-{2-[1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-ethylamino]-benzooxazol-6-yloxy}-pyridine-2-carboxylic acid methylamide.

출처 및 근거

ORD 기록
ord-d15b58a557bf4ac6900f2098326757fb
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710048B2

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