4-Fluoroaniline → HCID 68509777, compound

HRID 2241207Notes

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:61]=[CH:60][C:39]([CH2:40][N:41]2[C:45]3=[N:46][CH:47]=[CH:48][C:49]([O:50][C:51]4[CH:56]=[CH:55][C:54](N)=[CH:53][C:52]=4[CH3:58])=[C:44]3[C:43]([CH3:59])=[N:42]2)=[CH:38][CH:37]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:54]2[CH:55]=[CH:56][C:51]([O:50][C:49]3[CH:48]=[CH:47][N:46]=[C:45]4[N:41]([CH2:40][C:39]5[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:61][CH:60]=5)[N:42]=[C:43]([CH3:59])[C:44]=34)=[C:52]([CH3:58])[CH:53]=2)[C:9]([C:11]2([C:14]([NH2:31])=[O:16])[CH2:12][CH2:13]2)=[O:10])=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 97314-Fluoroaniline

HCID 690171,1-Cyclopropanedicarboxylic acid

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

HCID 68512984HCID 68512984, compound

Product 1

HCID 68509777HCID 68509777, compoundYield 11%

Procedure

Prepared from 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (0.2187 g, 0.6076 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-methylbenzenamine (0.091 g, 0.2430 mmol) according to the procedure of Example 13, Step C. The crude product was purified by preparative TLC (0.5 mm) eluting with EtOAc. The product (18 mg, 11%) was obtained as an orange solid. LRMS (esi pos) m/e 579 (M+1).

Workup

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

Sources & evidence

ORD record: ord-dd1a7eddfda04da2b1cb153d6dacda4a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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