3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamide dihydrochloride

HRID 500924Notes

Reaction equation

HRID 500924 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:24])[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]([C:18]3[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=3)[S:17][C:10]=12.[ClH:25].FC1C=C(N[C:51]([NH:53][C:54](=[O:62])[CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)=[O:52])C=CC=1OC1C=CN=C2C=C(C(N3CCCC3)=O)SC=12>>[ClH:25].[ClH:25].[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:51]([NH:53][C:54](=[O:62])[CH2:55][C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=2)=[O:52])[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]([C:18]3[N:19]=[CH:20][N:21]([CH3:23])[CH:22]=3)[S:17][C:10]=12

Participants

3

Reactant 2

HCID 594245073-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamineHCID 68694761N-(3-Fluoro-4-(2-(pyrrolidine-1-carbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamide hydrochloride

Product 1

HCID 68692732N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamide dihydrochlorideYield 54%

Procedure

Starting from the compound 177 (scheme 35) and following the procedure described above for the synthesis of compound 305a, title compound 305c was obtained in 54% yield as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.08(s, 1H), 10.67(s, 1H), 8.66 (d, 1H, J=6.2 Hz), 8.26(s, 1H), 8.21(s, 1H), 7.93(s, 1H), 7.85(dd, 1H, J1=12.9 Hz, J2=2.5 Hz), 7.53(t, 1H, J=8.8 Hz), 7.65(s, 1H), 7.48-7.45(m, 1H), 7.35-7.30(m, 4H), 7.28-7.24(m, 1H), 6.94(d, 1H, J=6.1 Hz), 3.79(s, 3H), 3.75(s, 2H). MS (m/z): 502.1(M+H) (found).

Sources & evidence

ORD record
ord-ec3e477008044834aa702d2e980875c3
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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