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

HRID 1676236Notes

Reaction equation

HRID 1676236 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20](OCC)=[O:21])[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.[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]1>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[C:20]([NH:34][CH2:33][CH2:32][N:29]2[CH2:30][CH2:31][O:26][CH2:27][CH2:28]2)=[O:21])[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

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 24983242Ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate

Product 1

HCID 24983243N1-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenyl)-N2-(2-morpholinoethyl)oxalamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-(3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)phenylamino)-2-oxoacetate (prepared in Example 2; 36 mg, 0.10 mmol) and 2-morpholinoethanamine (65 mg, 0.50 mmol) were heated to 60° C. for 18 hours. The mixture was diluted with diethyl ether (1 mL) and filtered. The white solid was washed with diethyl ether (3×2 mL). The solid was dried under high vacuum. The product was obtained as a white powder (17 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 9.50 (s, 1H), 8.52 (d, J=6 Hz, 1H), 7.99 (m, 1H), 7.87 (m, 1H), 7.76 (d, J=6 Hz, 1H), 7.58 (d, J=6 Hz, 1H), 7.41 (m, 1H), 7.29 (m, 1H), 6.52 (d, J=6 Hz, 1H), 3.74 (m, 4H), 3.49 (m, 2H), 2.59 (m, 2H), 2.50 (m, 4H). LRMS (ESI pos) m/e 445 (M+1). HPLC: 100% purity (220 nm).

Workup

  1. filtrationfiltered
  2. washThe white solid was washed with diethyl ether (3×2 mL)
  3. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-98f0b4aba302417a9c13e0501d99b8de
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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