3-Fluoroaniline → N1-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-N2-(3-fluorophenyl)oxalamide

HRID 1676238Notes

Reaction equation

HRID 1676238 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20]([O:22]CC)=O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[CH:16][S:17][C:10]=12.[F:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30]>>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20]([NH:30][C:29]2[CH:31]=[CH:32][CH:33]=[C:27]([F:26])[CH:28]=2)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[CH:16][S:17][C:10]=12

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 24983242Ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

Product 1

HCID 24983245N1-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-N2-(3-fluorophenyl)oxalamideYield 16.5%

Conditions

Temperature
100 °C

Procedure

Prepared from ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate (Example 2; 36 mg, 0.10 mmol) and 3-fluoroaniline (139 mg, 1.25 mmol) according to the procedure for Example 3, except the reaction was heated to 100° C. for 18 hours. The product was purified by preparative TLC (1:1 EtOAc/hexanes). The product was obtained as a white powder (7 mg, 6%). 1H NMR (400 MHz, CDCl3+MeOD-d3) δ 8.48 (d, J=6 Hz, 1H), 7.92 (m, 1H), 7.83 (d, J=6 Hz, 1H), 7.67 (m, 1H), 7.57 (d, J=6 Hz, 1H), 7.51 (m, 1H), 7.35 (m, 3H), 6.94 (m, 1H), 6.57 (d, J=6 Hz, 1H). LRMS (ESI pos) m/e 426 (M+1). HPLC: 97% purity (220 nm).

Workup

  1. customThe product was purified by preparative TLC (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-dfa9ae24ec234cb3a96a1c1209058dd0
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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