4-Fluoroaniline → HCID 67347151, compound

HRID 1676243Notes

Reaction equation

HRID 1676243 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[CH:17][S:18][C:11]=12)[NH2:5].FC1C=CC([NH:26][C:27]([C:29]2([C:32](O)=[O:33])[CH2:31][CH2:30]2)=[O:28])=CC=1.C1(C(O)=O)(C(O)=O)CC1.[F:44][C:45]1[CH:51]=[CH:50][C:48](N)=[CH:47][CH:46]=1>>[F:1][C:2]1[CH:3]=[C:4]([N:5]([C:48]2[CH:50]=[CH:51][C:45]([F:44])=[CH:46][CH:47]=2)[C:32]([C:29]2([C:27]([NH2:26])=[O:28])[CH2:30][CH2:31]2)=[O:33])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[CH:17][S:18][C:11]=12

Participants

5

Reactant 4

HCID 97314-FluoroanilineHCID 690171,1-Cyclopropanedicarboxylic acidHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 594244303-Fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)aniline

Product 1

HCID 67347151HCID 67347151, compoundYield 25%

Procedure

Prepared from 3-fluoro-4-(thieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 1, Step B; 130 mg, 0.50 mmol) and 1-((4-fluorophenyl)carbamoyl) -cyclopropanecarboxylic acid (123 mg, 0.550 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline using the methods described in WO 2005/030140 and by Shih and Rankin, Synth. Comm. 1996, 26(4), 833-836) according to the procedure described for Example 10. The crude was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (60 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 10.06 (s, 1H), 8.51 (s, 1H), 8.29 (s, 1H), 7.75 (m, 2H), 7.56 (d, J=5 Hz, 1H), 7.45 (m, 2H), 7.26 (m, 2H), 7.06 (m, 2H), 6.51 (d, J=5 Hz, 1H), 1.80 (m, 2H), 1.62 (m, 2H). LRMS (ESI pos) m/e 466 (M+1). HPLC: 97% purity (220 nm).

Workup

  1. customThe crude was purified by preparative TLC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-faed47a35685401984380c0a77924689
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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