4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 70681387, compound

HRID 1396205Notes

Reaction equation

HRID 1396205 reaction equation
[CH:1]1([NH:4][C:5](=[O:21])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15](Cl)[N:14]=2)[CH2:3][CH2:2]1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)[CH2:25][CH2:24]1>C(Cl)Cl.CO>[Cl:19][C:18]1[C:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:21])=[N:14][C:15]([NH:34][C:33]2[CH:32]=[CH:31][C:30]([CH2:29][N:26]3[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]3)=[CH:36][CH:35]=2)=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 59363110HCID 59363110, compound

Product 1

HCID 70681387HCID 70681387, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from N-cyclopropyl-2((2,5-dichloropyrimidin-4-yl)amino)benzamide and 4-((4-methylpiperazin-1-yl)methyl)aniline in 38% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.64 (d, 1H, J=8.5 Hz), 8.11 (s, 1H), 7.50 (d, 2H, J=8.2 Hz), 7.44 (m, 2H), 7.25 (d, 2H, J=8.2 Hz), 7.07 (t, 1H, J=7.5 Hz), 6.38 (bs, 1H), 3.50 (s, 2H), 2.93 (q, 1H, J=3.4 Hz), 2.55 (bs, 8H), 2.35 (s, 3H), 0.92 (m, 2H), 0.65 (m, 2H); MS (ESI): 492.1 [M+H]+.

Workup

  1. customaccording to synthesis procedure B
  2. temperaturegradually increasing to 95:5)

Sources & evidence

ORD record
ord-3b9d9fccd4ad463b93ea91cba33fc6e1
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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