1-Methylpiperazine → HCID 21905769, compound

HRID 1246816Notes

Reaction equation

HRID 1246816 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:9]1[N:17]=[C:16]([CH3:18])[N:15]=[C:14]2[C:10]=1[N:11]=[C:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[N:13]2[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1>C(O)C>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([N:13]2[C:12]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])=[N:11][C:10]3[C:14]2=[N:15][C:16]([CH3:18])=[N:17][C:9]=3[N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 21905776HCID 21905776, compound

Product 1

HCID 21905769HCID 21905769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-methylpiperazine (200 μl) in ethanol (0.8 ml) was added to 6-chloro-9-(4-chlorophenyl)-8-(2-fluorophenyl)-2-methyl-9H-purine I-(11A-1)c (24 mg, 0.06 mmol) and placed on a 60° C. shaker apparatus for 30 minutes. The reaction was loaded directly onto a TLC preparative plate for purification using 10% methanol/ethyl acetate as the solvent to obtain the desired title compound 11A-1: +ESI MS (M+1) 465. A solution of the material in methylene chloride/methanol was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 11A-1 (35 mg, quantitative): +ESI MS (M+1) 437.2; 1H NMR (400 MHz, CD3OD) δ 7.70–7.25 (br m, 7H), 7.09 (t, J=9.1 Hz, 1H), 5.80 (br s, 2H), 3.74 (br s, 4H), 3.36 (br s, 2H), 2.99 (s, 3H), 2.64 (s, 3H).

Workup

  1. customplaced on a 60° C.
  2. customfor 30 minutes
  3. customThe reaction was loaded directly onto a TLC preparative plate for purification

Sources & evidence

ORD record
ord-c5df4f8537fd4b5388ef72e383c8f2a7
Source dataset
uspto-grants-2006_10
Patent number
US07129239B2

Reaction notes

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