4-Fluoroaniline → HCID 68510647, compound

HRID 2241205Notes

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.[CH3:34][O:35][C:36]1[CH:62]=[CH:61][C:39]([CH2:40][N:41]2[C:45]3=[N:46][CH:47]=[CH:48][C:49]([O:50][C:51]4[C:56]([Cl:57])=[CH:55][C:54](N)=[CH:53][C:52]=4[Cl:59])=[C:44]3[C:43]([CH3:60])=[N:42]2)=[CH:38][CH:37]=1>>[Cl:59][C:52]1[CH:53]=[C:54]([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:55]=[C:56]([Cl:57])[C:51]=1[O:50][C:49]1[CH:48]=[CH:47][N:46]=[C:45]2[N:41]([CH2:40][C:39]3[CH:61]=[CH:62][C:36]([O:35][CH3:34])=[CH:37][CH:38]=3)[N:42]=[C:43]([CH3:60])[C:44]=12

Participants

Reactant 4

HCID 97314-Fluoroaniline

HCID 690171,1-Cyclopropanedicarboxylic acid

HCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

HCID 68515103HCID 68515103, compound

Product 1

HCID 68510647HCID 68510647, compoundYield 7%

Procedure

Prepared from 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (0.1354 g, 0.3762 mmol; prepared from cyclopropane-1,1-dicarboxylic acid and 4-fluoroaniline using the methods of WO 2005/030140 and by Shih and Rankin, Synth. Comm. 1996, 26(4), 833-836) and 4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3,5-dichlorobenzenamine (0.170 g, 0.1505 mmol) according to the procedure of Example 13, Step C. The crude product was purified preparative TLC (0.5 mm) eluting with EtOAc. Product (12 mg, 7%) was obtained as a orange solid. LRMS (esi pos) m/e 634 (M+1).

Workup

customThe crude product was purified preparative TLC (0.5 mm)
washeluting with EtOAc

Sources & evidence

ORD record: ord-eef785d15d674605a6d29a12468940c4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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