4-Fluoroaniline → N-(3-chloro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

HRID 1676274Notes

Reaction equation

HRID 1676274 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([I:18])[S:17][C:10]=12.FC1C=CC([NH:27][C:28]([C:30]2([C:33](O)=[O:34])[CH2:32][CH2:31]2)=[O:29])=CC=1.C1(C(O)=O)(C(O)=O)CC1.[F:45][C:46]1[CH:52]=[CH:51][C:49](N)=[CH:48][CH:47]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([N:19]([C:49]2[CH:51]=[CH:52][C:46]([F:45])=[CH:47][CH:48]=2)[C:33]([C:30]2([C:28]([NH2:27])=[O:29])[CH2:31][CH2:32]2)=[O:34])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([I:18])[S:17][C:10]=12

Participants

5

Reactant 4

HCID 97314-FluoroanilineHCID 690171,1-Cyclopropanedicarboxylic acidHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 67347138HCID 67347138, compound

Product 1

HCID 67349682N-(3-chloro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

Procedure

Prepared from 3-chloro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (0.300 g, 0.499 mmol) and 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (0.167 g, 0.749 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 for Example 72, Step B. The crude was purified by Biotage 40S (2:1EtOAc/Hexane). After concentration the product was a brown oil (160 mg, 26%). LRMS (ESI pos) m/e 608 (M+1).

Workup

  1. customThe crude was purified by Biotage 40S (2
  2. concentrationAfter concentration the product

Sources & evidence

ORD record
ord-d3d9ff95e0834fa68f26581b97653eb1
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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