4-Fluoroaniline → HCID 68814972, compound

HRID 1792622Notes

Reaction equation

HRID 1792622 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]=[CH:30][N:29]=[C:28]3[N:35]2[CH2:40][CH2:39][N:38]([C:41]3[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=3)[C:44](O)=[O:45])[CH2:37][CH2:36]2)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:50][C:51]1[CH:57]=[CH:56][C:54]([NH2:55])=[CH:53][CH:52]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[F:50][C:51]1[CH:57]=[CH:56][C:54]([NH:55][C:44](=[O:45])[C:43]2[CH:47]=[CH:48][CH:49]=[C:41]([N:38]3[CH2:39][CH2:40][N:35]([C:28]4[C:27]5[C:32](=[CH:33][CH:34]=[C:25]([C:22]6[CH:23]=[CH:24][N:20]([C:1]([C:2]7[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=7)([C:8]7[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=7)[C:14]7[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=7)[N:21]=6)[CH:26]=5)[N:31]=[CH:30][N:29]=4)[CH2:36][CH2:37]3)[CH:42]=2)=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68814121HCID 68814121, compound

Product 1

HCID 68814972HCID 68814972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg 3-{4-[6-(1-trityl-1H-pyrazolyl)-4-quinazolinyl]piperazin-1-yl} benzoic acid (compound in Example 829), 35 mg 4-fluoroaniline, 46 mg 1-hydroxybenzotriazole and 65 mg 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were dissolved in dichloromethane and stirred for about 12 hours, and the reaction solution was concentrated and purified by silica gel column chromatography to give N1-(4-fluorophenyl)-3-{4-[6-(1-trityl-1H-pyrazolyl)-4-quinazolinyl]piperazin-1-yl}benzamide.

Workup

  1. concentrationthe reaction solution was concentrated
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc9e7bb3637e4ecb84aad6ec92be418b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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