2-(Phenylcarbamoyl)acetic acid → N-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-oxo-1-phenylpyrrolidine-3-carboxamide

HRID 418662Notes

Reaction equation

HRID 418662 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:36])[CH2:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:28])=[CH:20][C:19]=3[F:37])[CH:9]=2)[N:5]=[CH:4]1)[CH3:2].O=[C:39](NC1C=CC=CC=1)[CH2:40]C(O)=O>>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([CH:26]4[CH2:40][CH2:39][N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:27]4=[O:28])=[O:36])=[CH:20][C:19]=3[F:37])[CH:9]=2)[N:5]=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 2565932-(Phenylcarbamoyl)acetic acidHCID 56953451N1-(4-(2-(1-ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-N3-phenylmalonamide

Product 1

HCID 16040360N-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-2-oxo-1-phenylpyrrolidine-3-carboxamideYield 40%

Procedure

Following the procedure described above for the synthesis of compound 5d (scheme 4), but replacing acid 1 with the acid 205, title compound 204 was obtained in 40% yield. 1HNMR (DMSO-d6) δ(ppm): 10.72 (s, 1H), 8.49 (d, J=5.7 Hz, 1H), 8.06 (d, J=1.0 Hz, 1H), 7.96-7.90 (m, 2H), 7.72 (s, 1H), 7.67-7.65 (m, 2H), 7.53-7.49 (m, 2H), 7.41-7.37 (m, 2H), 7.16 (t, J=7.2 Hz, 1H), 6.70 (d, J=5.5 Hz, 1H), 4.06 (q, 2H), 3.93 (m, 2H), 3.77 (t, J=8.2 Hz, 1H), 4.42 (m, 2H), 1.40 (t, 3H). MS (m/z): 542.0 (M+H).

Sources & evidence

ORD record
ord-cad177c0939d4d9eb5d07da80c1d2e5a
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

Loading…