N1-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamide → N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide

HRID 2193739Notes

Reaction equation

HRID 2193739 reaction equation
[CH3:1][N:2]([CH3:38])[NH:3][C:4]([C:6]1[S:14][C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:36])[CH2:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[O:26])=[CH:18][C:17]=2[F:37])[CH:7]=1)=[O:5].N[C:40]1C=CC(OC2C=CN=C3C=C(C(N(C)N(C)C)=O)SC=23)=C(F)C=1>>[F:37][C:17]1[CH:18]=[C:19]([NH:22][C:23](=[O:36])[CH2:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])=[O:26])[CH:20]=[CH:21][C:16]=1[O:15][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:7]=[C:6]([C:4]([N:3]([CH3:40])[N:2]([CH3:1])[CH3:38])=[O:5])[S:14][C:13]=12

Participants

3

Reactant 2

HCID 16040873N1-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamideHCID 587902027-(4-amino-2-fluorophenoxy)-N,N',N'-trimethylthieno[3,2-b]pyridine-2-carbohydrazide

Product 1

HCID 16040875N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamideYield 43%

Procedure

Following the procedure described above for compound 236 (step 4, example 95, scheme 63) but replacing amine 239 with 7-(4-amino-2-fluorophenoxy)-N,N′,N′-trimethylthieno[3,2-b]pyridine-2-carbohydrazide (244), title compound 241 was obtained in 43% yield. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.45 (s, 1H), 8.45 (d, J=5.4 Hz, 1H), 7.79 (d, J=13.3 Hz, 1H), 7.67 (s, 1H), 7.62-7.31 (m, 7H), 6.62 (d, J=5.4 Hz, 1H), 3.40 (s, 9H), 3.23 (s, 2H), 3.21 (s, 3H). MS (m/z): (M+1) 536.2 (100%).

Sources & evidence

ORD record
ord-8c4720c4e31344a4afc92fd9727dbd6e
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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