7-(4-amino-2-fluorophenoxy)-N,N',N'-trimethylthieno[3,2-b]pyridine-2-carbohydrazide → N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-methyl-N3-phenylmalonamide

HRID 418678Notes

Reaction equation

HRID 418678 reaction equation
CN(C)NC(C1SC2C(=NC=CC=2O[C:16]2[CH:21]=[CH:20][C:19]([N:22]([C:29]3C=CC=CC=3OC)[C:23](=[O:28])[CH2:24][C:25](N)=[O:26])=[CH:18][C:17]=2F)C=1)=O.[NH2:39][C:40]1[CH:62]=[CH:61][C:43]([O:44][C:45]2[CH:50]=[CH:49][N:48]=[C:47]3[CH:51]=[C:52]([C:54]([N:56]([CH3:60])[N:57]([CH3:59])[CH3:58])=[O:55])[S:53][C:46]=23)=[C:42]([F:63])[CH:41]=1>>[F:63][C:42]1[CH:41]=[C:40]([NH:39][C:25](=[O:26])[CH2:24][C:23]([N:22]([CH3:29])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:21][CH:20]=2)=[O:28])[CH:62]=[CH:61][C:43]=1[O:44][C:45]1[CH:50]=[CH:49][N:48]=[C:47]2[CH:51]=[C:52]([C:54]([N:56]([CH3:60])[N:57]([CH3:58])[CH3:59])=[O:55])[S:53][C:46]=12

Participants

3

Reactant 2

HCID 587902027-(4-amino-2-fluorophenoxy)-N,N',N'-trimethylthieno[3,2-b]pyridine-2-carbohydrazideHCID 66649285N'-(4-(2-(2,2-Dimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-(2-methoxyphenyl)malonamide

Product 1

HCID 66649054N1-(3-fluoro-4-(2-(1,2,2-trimethylhydrazinecarbonyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-methyl-N3-phenylmalonamideYield 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-6cf2ff1eadc345edb5c3a8c5742d4c5c
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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