4-(4-Methylpiperazin-1-yl)aniline → HCID 67478843, compound

HRID 472451Notes

Reaction equation

HRID 472451 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:15]1[C:16]2[N:17]([N:21]=[C:22](Cl)[N:23]=2)[CH:18]=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:15]1[C:16]2[N:17]([N:21]=[C:22]([NH:38][C:35]3[CH:34]=[CH:33][C:32]([N:29]4[CH2:28][CH2:27][N:26]([CH3:25])[CH2:31][CH2:30]4)=[CH:37][CH:36]=3)[N:23]=2)[CH:18]=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479012HCID 67479012, compound

Product 1

HCID 67478843HCID 67478843, compound

Procedure

170 b) 2-({2-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester was prepared from 2-[(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (400.0 mg, 1.137 mmol) and 4-(4-methyl-piperazin-1-yl)-phenylamine (240.0 mg, 1.255 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (63.0 mg, 0.115 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a tan resin (0.090 g, 16%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.81-7.74 (m, 1H), 7.47 (d, J=7.6 Hz, 2H), 6.95 (dm J=8.8 Hz, 2H), 6.74-6.45 (m, 3H), 5.40-4.90 (m, 1H), 4.23-4.06 (m, 1H), 3.56-3.05 (m, 8H), 2.63-2.57 (m, 4H), 2.36 (s, 3H), 2.05-1.80 (m, 4H), 1.56-1.44 (m, 9H). MS=507 (MH)+.

Sources & evidence

ORD record
ord-9e6025dd9d99443683a9fbfb3e86fb16
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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