4-Fluoroaniline → HCID 67346819, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([OH:16])=O)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C1(C(O)=O)(C(O)=O)CC1.FC1C=CC([NH2:31])=CC=1.[F:34][C:35]1[CH:36]=[C:37](N)[CH:38]=[CH:39][C:40]=1[O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44]2[CH:48]=[C:49]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[S:50][C:43]=12>>[F:34][C:35]1[CH:36]=[C:37]([N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([C:11]2([C:14]([NH2:31])=[O:16])[CH2:12][CH2:13]2)=[O:10])[CH:38]=[CH:39][C:40]=1[O:41][C:42]1[CH:47]=[CH:46][N:45]=[C:44]2[CH:48]=[C:49]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[S:50][C:43]=12Participants
Procedure
Prepared from 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (34.84 mg, 0.1561 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), and 3-fluoro-4-(2-phenylthieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 76, Step A; 35 mg, 0.1040 mmol) according to the procedure for Example 73. The product was purified by preparative TLC eluting with EtOAc/MeOH (9:1). Isolated the product as a light yellow oil, which solidified upon standing (4.3 mg, 8%). 1H NMR (CDCl3, 400 MHz) δ 10.03 (s, 1H), 8.47 (d, J=5.5 Hz, 1H), 8.27 (s, 1H), 7.77 (m, 3H), 7.46 (m, 5H), 7.24 (m, 2H), 7.06 (d, J=9.0 Hz, 2H), 6.49 (m, 2H) 1.80, (m, 2H), 1.62 (m, 2H). LRMS (APCI pos) m/e 542 (M+1).
Workup
- customThe product was purified by preparative TLC
- washeluting with EtOAc/MeOH (9:1)
Sources & evidence
- ORD record
- ord-8f4b4c54d8554e179dbfd3e45e9fba7e
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003662B2
Reaction notes
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