1-Methylhomopiperazine → HCID 22291682, compound

HRID 968116Notes

Reaction equation

HRID 968116 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:31]([Cl:34])=[CH:32][N:33]=1)[C:5]([NH:7][C:8]1[CH:30]=[CH:29][C:11]2[CH2:12][CH2:13][C:14]3[C:15]([C:26]([NH2:28])=[O:27])=[N:16][N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:18]=3[C:10]=2[CH:9]=1)=[O:6].[CH3:35][N:36]1[CH2:42][CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[Cl:34][C:31]1[C:4]([C:5]([NH:7][C:8]2[CH:30]=[CH:29][C:11]3[CH2:12][CH2:13][C:14]4[C:15]([C:26]([NH2:28])=[O:27])=[N:16][N:17]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=5)[C:18]=4[C:10]=3[CH:9]=2)=[O:6])=[CH:3][C:2]([N:39]2[CH2:40][CH2:41][CH2:42][N:36]([CH3:35])[CH2:37][CH2:38]2)=[N:33][CH:32]=1

Participants

3

Reactant 2

HCID 2283491-MethylhomopiperazineHCID 22291629HCID 22291629, compound

Product 1

HCID 22291682HCID 22291682, compoundYield 78.3%

Procedure

The title compound was synthesized by the same procedure as in Example 214 starting with the title compound of Example 248 (1 g, 0.0020 mol) and 1-methylhomopiperazine (4.6 g, 0.040 mol). The reaction was run at 95° C. for 24 h. After allowing the reaction mixture to cool, the volatiles were removed under vacuum. The residue was triturated with H2O to yield 0.899 g of the title compound as a tetrahydrate (yield: 71%). 1H NMR (300 MHz, d6-DMSO): δ 1.81-1.83 (m, 2H), 2.21 (s, 3H), 2.41 (t, 2H, J=5.5 Hz), 2.53 (t, 2H, J=4.56 Hz), 2.87-2.93 (m, 4H), 3.53 (t, 2H, J=5.5 Hz), 3.63-3.67 (m, 2H), 6.62 (s, 1H), 7.19 (d, 1H, J=1.9 Hz), 7.27-7.38 (m, 4H), 7.42-7.45 (dd, 1H, J=8.12 Hz, 1.88 Hz), 7.53-7.58 (m, 3H), 8.07 (s, 1H), 10.31 (s, 1H). M+1=575.

Workup

  1. temperatureto cool
  2. customthe volatiles were removed under vacuum
  3. customThe residue was triturated with H2O

Sources & evidence

ORD record
ord-411142497fa84ad39d9dcead208dc7c4
Source dataset
uspto-grants-2005_10
Patent number
US06956052B2

Reaction notes

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