N-methyl-N-(1-methylpiperidin-4-yl)benzene-1,4-diamine → HCID 66576946, compound

HRID 1396199Notes

Reaction equation

HRID 1396199 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[C:5]([CH3:16])=[CH:4][N:3]=1.[CH3:17][N:18]([CH:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1)[C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>C(Cl)Cl.CO>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH3:16])=[CH:4][N:3]=[C:2]([NH:25][C:22]3[CH:21]=[CH:20][C:19]([N:18]([CH3:17])[CH:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)=[CH:24][CH:23]=3)[N:7]=2)[CH:13]=[CH:12][C:11]=1[F:14]

Participants

4

Reactant 2

HCID 16795276N-methyl-N-(1-methylpiperidin-4-yl)benzene-1,4-diamineHCID 86673359HCID 86673359, compound

Product 1

HCID 66576946HCID 66576946, compoundYield 25%

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-fluorophenyl)-5-methylpyrimidine and N1-methyl-N1-(1-methylpiperidin-4-yl)benzene-1,4-diamine in 25% yield (yellow solid) after flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.24 (s, 1H), 7.69 (dd, 1H, J=7.2, 1.7 Hz), 7.49 (m, 1H), 7.41 (d, 2H, J=8.9 Hz), 7.20 (d, 1H, 8.5 Hz), 6.79 (d, 2H, J=8.5 Hz), 3.49 (m, 1H), 3.00 (d, 2H, J=10.6 Hz), 2.74 (s, 3H), 2.34 (s, 3H), 2.21 (s, 3H), 2.11 (m, 2H), 1.89 (m, 2H), 1.72 (d, 2H, J=11.6 Hz); MS (ESI): 440.3 [M+H]+, 220.8 [M+2H]2+.

Workup

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

Sources & evidence

ORD record
ord-f2d5e1ff4cee40a2b8bde8615354e150
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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