1-(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamine → 4-(2-(3-((Dimethylamino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 2193718

Reaction equation

HRID 2193718 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-])=O)[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[C:16]([CH2:20][N:21]([CH3:23])[CH3:22])[CH:17]=[CH:18][CH:19]=3)[S:13][C:6]=12.NC1C=CC(OC2C=CN=C3C=C(C(N4CCCC4)=O)SC=23)=C(F)C=1>>[CH3:23][N:21]([CH2:20][C:16]1[CH:15]=[C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:24]=[CH:25][C:26]([NH2:28])=[CH:27][C:2]=3[F:1])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1)[CH3:22]

Participants

3

Reactant 2

HCID 587902811-(3-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)-N,N-dimethylmethanamineHCID 59424653(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 587901024-(2-(3-((Dimethylamino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineYield 44%

Procedure

Starting from the compound 149 and following the same procedure as described above for the synthesis of compound 23 (scheme 6), title compound 150 was obtained in 44% yield MS (m/z): 394.0 (M+H).

Sources & evidence

ORD record
ord-63709ff0617b495f9edc436fe8169e99
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Linked notes

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