2-Methyl-3-oxo-3-(phenylamino)propanoic acid → N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-methyl-N3-phenylmalonamide

HRID 418599Notes

Reaction equation

HRID 418599 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]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12.FC1C=C(NC(=O)CC(NC2C=CC=CC=2OC)=O)C=CC=1OC1C=CN=C2C=C(C3N(C)C=CN=3)SC=12.COC1C=CC=CC=1NC(=O)CC(O)=O.[CH3:78][CH:79]([C:83](=[O:91])[NH:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[C:80](O)=[O:81]>>[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:80](=[O:81])[CH:79]([CH3:78])[C:83]([NH:84][C:85]2[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=2)=[O:91])[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]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12

Participants

5

Reactant 4

HCID 126058802-Methyl-3-oxo-3-(phenylamino)propanoic acidHCID 12664594N-(2-Methoxy-phenyl)-malonamic acidHCID 16040869N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamideHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 16041061N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-methyl-N3-phenylmalonamide

Procedure

Starting from the amine 9 and following the procedure described above for compound 28a (example 8, step 2) but substituting acid 27 for the acid 37, title compound 38 was obtained as a white solid (20% yield). 1H NMR (d6-DMSO) δ (ppm): 10.99 (s, 1H), 10.51 (s, 1H), 8.64 (d. 1H), 8.25 (s, 1H), 7.94 (s, 1H), 7.80 (s, 1H), 7.65 (d, 2H) 7.57-7.48 (m, 2H), 7.28 (t, 2H), 7.03 (t, 1H), 6.88 (d, 1H), 4.08 (s, 3H), 1.18 (s, 3H). MS (m/z): 516.1 (M+H).

Sources & evidence

ORD record
ord-a22b275402b343048a1d6ed0faa830c7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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