4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine → N1-(4-(2-(1-ethyl-1H-imidazole-4-carbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-fluorophenyl)malonamide

HRID 2193666Notes

Reaction equation

HRID 2193666 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:25](=[O:38])[CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2OF)=[O:28])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16](C3N(C)C=CN=3)[S:17][C:10]=12.[F:39]C1C=C(N)C=CC=1OC1C=CN=C2C=C(C3N(C)C=CN=3)SC=12.[CH2:63]([N:65]1[CH:69]=[C:68](C2SC3C(=NC=CC=3OC3C=CC(N)=CC=3F)C=2)[N:67]=[CH:66]1)[CH3:64]>>[CH2:63]([N:65]1[CH:69]=[C:68]([C:16]2[S:17][C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[O:8][C:7]3[CH:6]=[CH:5][C:4]([NH:24][C:25](=[O:38])[CH2:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[F:39])=[O:28])=[CH:3][C:2]=3[F:1])[CH:15]=2)[N:67]=[CH:66]1)[CH3:64]

Participants

4

Reactant 3

HCID 594244554-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamineHCID 66648945n1-(3-Fluoro-4-(2-(1-methyl-1h-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-n3-(2-fluoroxyphenyl)malonamide

Product 1

HCID 16041962N1-(4-(2-(1-ethyl-1H-imidazole-4-carbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-fluorophenyl)malonamideYield 42%

Procedure

Following the procedure described above for the compound 30a (example 12, step 2) but substituting amine 9 for the amine 15, title compound 30b was obtained in 42% yield. 1H NMR (DMSO-d6) δ (ppm): 10.55 (s, 1H), 10.05 (s, 1H), 8.41 (d, 1H), 7.97 (m, 1H), 7.95 (s, 1H), 7.85 (dd, 1H), 7.77 (d, 1H), 7.65 (s, 1H), 7.45 (dd, 1H), 7.41 (dd, 1H), 7.26 (m, 1H), 7.16 (m, 1H), 6.57 (d, 1H), 4.03 (q, 2H), 3.60 (s, 2H), 1.38 (t, 3H). MS (m/z): 534.0 (M+H).

Sources & evidence

ORD record
ord-4ee9955d4bb5494a9d051d1a0fb26d80
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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