4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 70687738, compound

HRID 1396188Notes

Reaction equation

HRID 1396188 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Cl:16])[CH:10]=2)[C:5]([CH3:17])=[CH:4][N:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1>C(Cl)Cl.CO>[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[F:15])[O:8][C:6]1[C:5]([CH3:17])=[CH:4][N:3]=[C:2]([NH:30][C:29]2[CH:28]=[CH:27][C:26]([CH2:25][N:22]3[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]3)=[CH:32][CH:31]=2)[N:7]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 79075741HCID 79075741, compound

Product 1

HCID 70687738HCID 70687738, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-chloro-4-(3-chloro-4-fluorophenoxy)-5-methylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 59% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ H 8.10 (s, 1H), 7.43 (t, 1H, J=8.4 Hz), 7.23 (d, 2H), 7.09 (d, 2H, J=8.2 Hz), 7.04 (dd, 1H, J=9.6, 2.4 Hz), 6.94 (m, 1H), 3.42 (s, 2H), 2.46 (bs, 8H) 2.27 (s, 3H), 2.18 (s, 3H); MS (ESI): 442.3 [M+H]+, 221.7 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-a752f57085b94e4084fc241d6f7e0169
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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