4-Fluoroaniline → HCID 68514261, compound

HRID 2241203Notes

Reaction equation

HRID 2241203 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]([CH3:57])=[CH:55][C:54](N)=[C:53]([Cl:59])[CH:52]=4)=[C:44]3[C:43]([CH3:60])=[N:42]2)=[CH:38][CH:37]=1>>[Cl:59][C:53]1[CH:52]=[C:51]([O:50][C:49]2[CH:48]=[CH:47][N:46]=[C:45]3[N:41]([CH2:40][C:39]4[CH:61]=[CH:62][C:36]([O:35][CH3:34])=[CH:37][CH:38]=4)[N:42]=[C:43]([CH3:60])[C:44]=23)[C:56]([CH3:57])=[CH:55][C:54]=1[N:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([C:11]1([C:14]([NH2:31])=[O:16])[CH2:12][CH2:13]1)=[O:10]

Participants

5

Reactant 4

HCID 97314-FluoroanilineHCID 690171,1-Cyclopropanedicarboxylic acidHCID 210815301-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic AcidHCID 68514705HCID 68514705, compound

Product 1

HCID 68514261HCID 68514261, compoundYield 17%

Procedure

Prepared from 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (0.1796 g, 0.4989 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)-2-chloro-5-methylbenzenamine (0.170 g, 0.1996 mmol) according to the procedure of Example 13, Step C. Purified by preparative TLC (0.5 mm) eluting with EtOAc. The product (23 mg, 17%) was obtained as an orange solid. LRMS (esi pos) m/e 614 (M+1).

Workup

  1. customPurified by preparative TLC (0.5 mm)
  2. washeluting with EtOAc

Sources & evidence

ORD record
ord-8c0a55d6eb9e4c39a3edf47eab97d128
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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