4-[[2-[5-[[Boc(2-methoxyethyl)amino]methyl]-2-pyridyl]-7-thieno[3,2-b]pyridyl]oxy]-3-fluoroaniline → 4-((2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)-3-fluoroaniline

HRID 84382Notes

Reaction equation

HRID 84382 reaction equation
NC1C=CC(OC2C=CN=C3C=C(C4N=CC(CN(CCOC)C(=O)OC(C)(C)C)=CC=4)SC=23)=C(F)C=1.[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[C:43]1[CH:44]=[CH:45][C:46]([C:49]2[S:57][C:56]3[C:51](=[N:52][CH:53]=[CH:54][C:55]=3[O:58][C:59]3[CH:64]=[CH:63][C:62]([N+:65]([O-])=O)=[CH:61][C:60]=3[F:68])[CH:50]=2)=[N:47][CH:48]=1>>[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[C:43]1[CH:44]=[CH:45][C:46]([C:49]2[S:57][C:56]3[C:51](=[N:52][CH:53]=[CH:54][C:55]=3[O:58][C:59]3[CH:64]=[CH:63][C:62]([NH2:65])=[CH:61][C:60]=3[F:68])[CH:50]=2)=[N:47][CH:48]=1

Participants

3

Reactant 2

HCID 579194724-[[2-[5-[[Boc(2-methoxyethyl)amino]methyl]-2-pyridyl]-7-thieno[3,2-b]pyridyl]oxy]-3-fluoroanilineHCID 579194962-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 579195224-((2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)-3-fluoroanilineYield 95%

Procedure

Following the procedure described above for the synthesis of compound 126 (Scheme 6) but substituting compound 125 for compound 138, title compound 139 was obtained in 95% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.68 (d, J=1.8 Hz, 1H), 8.50 (d, J=5.5 Hz, 1H), 8.36 (s, 1H), 8.29 (d, J=8.2 Hz, 1H), 7.96 (dd, J=8.2, 2.0 Hz, 1H), 7.11 (t, J=9.0 Hz, 1H), 6.60 (d, J=5.3 Hz, 1H), 6.53 (dd, J=13.1, 2.5 Hz, 1H), 6.44 (dd, J=8.7, 1.9 Hz, 1H), 5.87 (s, 1H), 5.55 (s, 2H), 4.11-4.07 (m, 2H), 4.00-3.97 (m, 2H). MS (m/z): 410.2 (M+H).

Sources & evidence

ORD record
ord-993b78ab2aa649b9a5a388b66dc94e50
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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